CN102241680A - 作为大麻素受体1活性抑制剂的化合物和组合物 - Google Patents
作为大麻素受体1活性抑制剂的化合物和组合物 Download PDFInfo
- Publication number
- CN102241680A CN102241680A CN2011101210450A CN201110121045A CN102241680A CN 102241680 A CN102241680 A CN 102241680A CN 2011101210450 A CN2011101210450 A CN 2011101210450A CN 201110121045 A CN201110121045 A CN 201110121045A CN 102241680 A CN102241680 A CN 102241680A
- Authority
- CN
- China
- Prior art keywords
- phenyl
- chloro
- dihydro
- pyrazolo
- pyrimidin
- Prior art date
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 201
- 239000000203 mixture Substances 0.000 title claims description 111
- 239000003112 inhibitor Substances 0.000 title abstract description 20
- 230000000694 effects Effects 0.000 title abstract description 19
- 102100033868 Cannabinoid receptor 1 Human genes 0.000 title abstract 4
- 101710187010 Cannabinoid receptor 1 Proteins 0.000 title abstract 4
- 238000000034 method Methods 0.000 claims abstract description 71
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
- 201000010099 disease Diseases 0.000 claims abstract description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 270
- 150000002367 halogens Chemical class 0.000 claims description 270
- -1 Phenyl Chemical group 0.000 claims description 269
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 155
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 141
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 91
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 88
- 229910052739 hydrogen Inorganic materials 0.000 claims description 86
- 239000001257 hydrogen Substances 0.000 claims description 86
- 150000002431 hydrogen Chemical class 0.000 claims description 80
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 70
- 239000000460 chlorine Substances 0.000 claims description 61
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 60
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 38
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 38
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 37
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 36
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 32
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 28
- 150000003851 azoles Chemical class 0.000 claims description 28
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 28
- 229910052794 bromium Inorganic materials 0.000 claims description 28
- 125000004076 pyridyl group Chemical group 0.000 claims description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 24
- 125000002541 furyl group Chemical group 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000004193 piperazinyl group Chemical group 0.000 claims description 23
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 23
- 239000011737 fluorine Substances 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 22
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 102000005962 receptors Human genes 0.000 claims description 19
- 108020003175 receptors Proteins 0.000 claims description 19
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 235000013305 food Nutrition 0.000 claims description 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 17
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 16
- GDZQGHGCKKWNAC-UHFFFAOYSA-N 1-phenyl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=2C(O)=NC=NC=2N1C1=CC=CC=C1 GDZQGHGCKKWNAC-UHFFFAOYSA-N 0.000 claims description 15
- 208000030814 Eating disease Diseases 0.000 claims description 15
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 15
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 15
- 235000014632 disordered eating Nutrition 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 208000008589 Obesity Diseases 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 230000037406 food intake Effects 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 235000020824 obesity Nutrition 0.000 claims description 14
- 125000005936 piperidyl group Chemical group 0.000 claims description 13
- 125000005493 quinolyl group Chemical group 0.000 claims description 13
- CSOYDALHEQEMAK-UHFFFAOYSA-N 2h-pyrimidine-1-carboxylic acid Chemical compound OC(=O)N1CN=CC=C1 CSOYDALHEQEMAK-UHFFFAOYSA-N 0.000 claims description 12
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 12
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 12
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 239000011630 iodine Substances 0.000 claims description 12
- 229940095102 methyl benzoate Drugs 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 11
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 10
- XIIVQDVEYVUNGQ-UHFFFAOYSA-N N=1CN(C=CC1)C1=CC=CC=C1C(=O)N Chemical class N=1CN(C=CC1)C1=CC=CC=C1C(=O)N XIIVQDVEYVUNGQ-UHFFFAOYSA-N 0.000 claims description 9
- 230000001404 mediated effect Effects 0.000 claims description 9
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 9
- 239000012453 solvate Substances 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 230000001225 therapeutic effect Effects 0.000 claims description 9
- 125000006655 (C3-C8) heteroaryl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 6
- DBMLEINSSMNUFA-UHFFFAOYSA-N CN(C(=O)N)N=O.N=1CN(C=CC1)C(=O)O Chemical compound CN(C(=O)N)N=O.N=1CN(C=CC1)C(=O)O DBMLEINSSMNUFA-UHFFFAOYSA-N 0.000 claims description 6
- 206010008190 Cerebrovascular accident Diseases 0.000 claims description 6
- 206010019196 Head injury Diseases 0.000 claims description 6
- AYDQIZKZTQHYIY-UHFFFAOYSA-N OC(=O)C1(C)CC(C(O)=O)=CC=C1 Chemical compound OC(=O)C1(C)CC(C(O)=O)=CC=C1 AYDQIZKZTQHYIY-UHFFFAOYSA-N 0.000 claims description 6
- 208000006011 Stroke Diseases 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 125000006226 butoxyethyl group Chemical group 0.000 claims description 6
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 6
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 6
- UEWVYZWCMJCHRT-UHFFFAOYSA-N n-fluoronitramide Chemical compound [O-][N+](=O)NF UEWVYZWCMJCHRT-UHFFFAOYSA-N 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000003944 tolyl group Chemical group 0.000 claims description 6
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- CBOQYUWSGVWBCH-UHFFFAOYSA-N 4-$l^{1}-oxidanylpyridine Chemical compound O=C1C=CN=C[CH]1 CBOQYUWSGVWBCH-UHFFFAOYSA-N 0.000 claims description 5
- VRPOMJYPGABUIY-UHFFFAOYSA-N 6-(4-bromophenyl)-2-methyl-5-(4-methylphenyl)-3-phenylpyrazolo[4,3-d]pyrimidin-7-one Chemical class C1=CC(C)=CC=C1C(N(C(=O)C1=NN2C)C=3C=CC(Br)=CC=3)=NC1=C2C1=CC=CC=C1 VRPOMJYPGABUIY-UHFFFAOYSA-N 0.000 claims description 5
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 208000028017 Psychotic disease Diseases 0.000 claims description 5
- 201000009032 substance abuse Diseases 0.000 claims description 5
- KWADLQINXZGEPT-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(2-fluorophenyl)-9-phenylpurin-6-one Chemical compound FC1=CC=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 KWADLQINXZGEPT-UHFFFAOYSA-N 0.000 claims description 4
- YJVARSALAHOUNO-UHFFFAOYSA-N 1-(4-bromophenyl)-8-ethyl-9-phenyl-2-[4-(trifluoromethyl)phenyl]purin-6-one Chemical compound C=1C=CC=CC=1N1C(CC)=NC(C(N2C=3C=CC(Br)=CC=3)=O)=C1N=C2C1=CC=C(C(F)(F)F)C=C1 YJVARSALAHOUNO-UHFFFAOYSA-N 0.000 claims description 4
- CNLORCDLZNDEQX-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-(methoxymethyl)phenyl]-9-phenylpurin-6-one Chemical compound C1=CC(COC)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 CNLORCDLZNDEQX-UHFFFAOYSA-N 0.000 claims description 4
- ILTJFHCMDXYBCB-UHFFFAOYSA-N 2-[4-(6-aminopyridin-3-yl)phenyl]-1-(4-chlorophenyl)-9-phenylpurin-6-one Chemical compound C1=NC(N)=CC=C1C1=CC=C(C=2N(C(=O)C=3N=CN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C=C1 ILTJFHCMDXYBCB-UHFFFAOYSA-N 0.000 claims description 4
- BFKYQYMHJANOTR-UHFFFAOYSA-N 2h-pyrimidine-1-carbonitrile Chemical compound N#CN1CN=CC=C1 BFKYQYMHJANOTR-UHFFFAOYSA-N 0.000 claims description 4
- NHDVULQHKIETPA-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-phenyl-6-[4-(1h-pyrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(C=2NN=CC=2)C=C1 NHDVULQHKIETPA-UHFFFAOYSA-N 0.000 claims description 4
- FEPKWKMQGCNDKH-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-[4-(2-chloropyrimidin-4-yl)phenyl]-3-methylsulfonyl-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=2N=C(C=3C=CC(=CC=3)C=3N=C(Cl)N=CC=3)N(C=3C=CC(Cl)=CC=3)C(=O)C=2C(S(=O)(=O)C)=NN1C1=CC=CC=C1 FEPKWKMQGCNDKH-UHFFFAOYSA-N 0.000 claims description 4
- SXNAFSAXVGSMRS-UHFFFAOYSA-N 6-[4-(2-aminopyrimidin-4-yl)phenyl]-5-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound NC1=NC=CC(C=2C=CC(=CC=2)C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=N1 SXNAFSAXVGSMRS-UHFFFAOYSA-N 0.000 claims description 4
- NALVOHWSZGQGAM-UHFFFAOYSA-N 6-[4-(2-aminopyrimidin-4-yl)phenyl]-5-(4-chlorophenyl)-3-methylsulfonyl-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=2N=C(C=3C=CC(=CC=3)C=3N=C(N)N=CC=3)N(C=3C=CC(Cl)=CC=3)C(=O)C=2C(S(=O)(=O)C)=NN1C1=CC=CC=C1 NALVOHWSZGQGAM-UHFFFAOYSA-N 0.000 claims description 4
- HXOKFCNYKJYTEM-UHFFFAOYSA-N 9-phenyl-3h-purin-6-one Chemical compound C1=NC=2C(=O)N=CNC=2N1C1=CC=CC=C1 HXOKFCNYKJYTEM-UHFFFAOYSA-N 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 208000026139 Memory disease Diseases 0.000 claims description 4
- 208000019695 Migraine disease Diseases 0.000 claims description 4
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 4
- 208000010877 cognitive disease Diseases 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 208000024908 graft versus host disease Diseases 0.000 claims description 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 4
- 230000005980 lung dysfunction Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 208000030159 metabolic disease Diseases 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- 206010027599 migraine Diseases 0.000 claims description 4
- 201000001119 neuropathy Diseases 0.000 claims description 4
- 230000007823 neuropathy Effects 0.000 claims description 4
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 231100000736 substance abuse Toxicity 0.000 claims description 4
- 208000011117 substance-related disease Diseases 0.000 claims description 4
- ABWSEZBDTUKXIQ-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(4-methylphenyl)-9-phenylpurin-6-one Chemical compound C1=CC(C)=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 ABWSEZBDTUKXIQ-UHFFFAOYSA-N 0.000 claims description 3
- HTKYPUUZJHYLPU-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(4-iodophenyl)-9-phenylpurin-6-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(N=CN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(I)C=C1 HTKYPUUZJHYLPU-UHFFFAOYSA-N 0.000 claims description 3
- RBUXSPCPIIMKJJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-(6-oxo-1h-pyridin-3-yl)phenyl]-9-phenylpurin-6-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(N=CN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(C2=CNC(=O)C=C2)C=C1 RBUXSPCPIIMKJJ-UHFFFAOYSA-N 0.000 claims description 3
- LNVUMXKSQYMVSZ-UHFFFAOYSA-N 1-(4-chlorophenyl)-6-oxo-9-phenyl-2-[4-(trifluoromethyl)phenyl]purine-8-carbonitrile Chemical compound C1=CC(C(F)(F)F)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=C(C#N)N2C1=CC=CC=C1 LNVUMXKSQYMVSZ-UHFFFAOYSA-N 0.000 claims description 3
- GLAABERGSQZJGM-UHFFFAOYSA-N 1-(4-chlorophenyl)-8-[ethyl(methyl)amino]-9-phenyl-2-[4-(trifluoromethyl)phenyl]purin-6-one Chemical compound C=1C=CC=CC=1N1C(N(C)CC)=NC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2C1=CC=C(C(F)(F)F)C=C1 GLAABERGSQZJGM-UHFFFAOYSA-N 0.000 claims description 3
- RWVSPZGSKDCFTL-UHFFFAOYSA-N 1-(4-chlorophenyl)-9-phenyl-2-(4-pyridin-4-ylphenyl)purin-6-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(N=CN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(C=2C=CN=CC=2)C=C1 RWVSPZGSKDCFTL-UHFFFAOYSA-N 0.000 claims description 3
- OPOQCSIYRBSSBR-UHFFFAOYSA-N 1-(4-chlorophenyl)-9-phenyl-2-(4-thiophen-3-ylphenyl)purin-6-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(N=CN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(C2=CSC=C2)C=C1 OPOQCSIYRBSSBR-UHFFFAOYSA-N 0.000 claims description 3
- NYBVWEFWLFHTAB-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(2-fluorophenyl)-1-(morpholine-4-carbonyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1C=NN2C(=O)N1CCOCC1 NYBVWEFWLFHTAB-UHFFFAOYSA-N 0.000 claims description 3
- MPOVKTNHXPTCBD-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(4-chlorophenyl)-3-phenyltriazolo[4,5-d]pyrimidin-7-one Chemical class C1=CC(Cl)=CC=C1N1C(=O)C(N=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(Br)C=C1 MPOVKTNHXPTCBD-UHFFFAOYSA-N 0.000 claims description 3
- OBSGRCRYWAXULL-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(4-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C)=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 OBSGRCRYWAXULL-UHFFFAOYSA-N 0.000 claims description 3
- FUXHFUZLVSJXKQ-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-phenyl-6-(4-phenylpiperazin-1-yl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1N1CCN(C=2C=CC=CC=2)CC1 FUXHFUZLVSJXKQ-UHFFFAOYSA-N 0.000 claims description 3
- MVGZQHBNCHWICT-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-phenyl-6-(4-pyridin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(C=2C=CN=CC=2)C=C1 MVGZQHBNCHWICT-UHFFFAOYSA-N 0.000 claims description 3
- SDDCGNXFPLCMTN-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-phenyl-6-[4-(1h-1,2,4-triazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(C=2NN=CN=2)C=C1 SDDCGNXFPLCMTN-UHFFFAOYSA-N 0.000 claims description 3
- UFWZQNVRLMZAJW-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(4-iodophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(I)C=C1 UFWZQNVRLMZAJW-UHFFFAOYSA-N 0.000 claims description 3
- ZUEHJLMCNBXRJT-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(4-methylphenoxy)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C)=CC=C1OC(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 ZUEHJLMCNBXRJT-UHFFFAOYSA-N 0.000 claims description 3
- RVQDJZFMMGKQHZ-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(4-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 RVQDJZFMMGKQHZ-UHFFFAOYSA-N 0.000 claims description 3
- PLSMUDWFPDRGDV-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-[4-(3-fluorophenyl)phenyl]-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC(C=2C=CC(=CC=2)C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=C1 PLSMUDWFPDRGDV-UHFFFAOYSA-N 0.000 claims description 3
- KOYWLFQAJOMUTN-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-[4-(6-oxo-1h-pyridin-3-yl)phenyl]-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(C2=CNC(=O)C=C2)C=C1 KOYWLFQAJOMUTN-UHFFFAOYSA-N 0.000 claims description 3
- CNBXMJSADODHEG-UHFFFAOYSA-N 6-(4-acetylphenyl)-5-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C(=O)C)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 CNBXMJSADODHEG-UHFFFAOYSA-N 0.000 claims description 3
- OEEJLILFNQTPJG-UHFFFAOYSA-N 6-(4-bromophenyl)-1-methyl-5-(4-methylphenyl)-3-phenylpyrazolo[4,3-d]pyrimidin-7-one Chemical class C1=CC(C)=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1N(C)N=C2C1=CC=CC=C1 OEEJLILFNQTPJG-UHFFFAOYSA-N 0.000 claims description 3
- LLWGEJHKYINBQU-UHFFFAOYSA-N 6-(4-bromophenyl)-5-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(Br)C=C1 LLWGEJHKYINBQU-UHFFFAOYSA-N 0.000 claims description 3
- JHHLKOVODNJNOM-UHFFFAOYSA-N 6-(4-bromophenyl)-5-(4-methylphenyl)-3-phenyl-1h-pyrazolo[4,3-d]pyrimidin-7-one Chemical class C1=CC(C)=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1NN=C2C1=CC=CC=C1 JHHLKOVODNJNOM-UHFFFAOYSA-N 0.000 claims description 3
- BNDXMOGJCSPPRR-UHFFFAOYSA-N 6-[4-(2-butoxyethyl)phenyl]-5-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(CCOCCCC)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 BNDXMOGJCSPPRR-UHFFFAOYSA-N 0.000 claims description 3
- MUCGSWNNGCNWKI-UHFFFAOYSA-N 6-[4-(4-aminopyridin-2-yl)phenyl]-5-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound NC1=CC=NC(C=2C=CC(=CC=2)C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=C1 MUCGSWNNGCNWKI-UHFFFAOYSA-N 0.000 claims description 3
- QCZZLDSJIBOZKL-UHFFFAOYSA-N 6-[4-(6-aminopyridin-3-yl)phenyl]-5-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=NC(N)=CC=C1C1=CC=C(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C=C1 QCZZLDSJIBOZKL-UHFFFAOYSA-N 0.000 claims description 3
- TYTOPSLDIBYYMY-UHFFFAOYSA-N 6-[4-[(2-aminocyclohexyl)amino]phenyl]-5-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound NC1CCCCC1NC1=CC=C(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C=C1 TYTOPSLDIBYYMY-UHFFFAOYSA-N 0.000 claims description 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 3
- BISPOJCBUUNWFO-UHFFFAOYSA-N BrC1=CC=C(C=C1)C1=CC=CC=C1N1N=CC(C1C1=CC=C(C=C1)Cl)=O Chemical compound BrC1=CC=C(C=C1)C1=CC=CC=C1N1N=CC(C1C1=CC=C(C=C1)Cl)=O BISPOJCBUUNWFO-UHFFFAOYSA-N 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000004064 dysfunction Effects 0.000 claims description 3
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 3
- WTXIVQKGPUYREK-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(2-methylphenyl)-9-phenylpurin-6-one Chemical compound CC1=CC=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 WTXIVQKGPUYREK-UHFFFAOYSA-N 0.000 claims description 2
- YSWZCFCTKUTUAD-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(3-fluorophenyl)-9-phenylpurin-6-one Chemical compound FC1=CC=CC(C=2N(C(=O)C=3N=CN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Br)=CC=2)=C1 YSWZCFCTKUTUAD-UHFFFAOYSA-N 0.000 claims description 2
- NSFGXVRAAXFIHT-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(4-chlorophenyl)-7-phenylpurin-6-one Chemical compound C1=CC(Cl)=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1N(C=1C=CC=CC=1)C=N2 NSFGXVRAAXFIHT-UHFFFAOYSA-N 0.000 claims description 2
- FCUNMFYODCOLGK-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(4-chlorophenyl)-9-phenylpurin-6-one Chemical compound C1=CC(Cl)=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 FCUNMFYODCOLGK-UHFFFAOYSA-N 0.000 claims description 2
- JEXJTVGJOUGEIK-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(4-ethylphenyl)-9-phenylpurin-6-one Chemical compound C1=CC(CC)=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 JEXJTVGJOUGEIK-UHFFFAOYSA-N 0.000 claims description 2
- HKRQWMFEHPCYOR-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(4-fluoro-3-methylphenyl)-9-phenylpurin-6-one Chemical compound C1=C(F)C(C)=CC(C=2N(C(=O)C=3N=CN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Br)=CC=2)=C1 HKRQWMFEHPCYOR-UHFFFAOYSA-N 0.000 claims description 2
- OQRSWWCIZIRDKL-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(4-methylphenyl)-6-oxo-9-phenylpurine-8-carbonitrile Chemical compound C1=CC(C)=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1N=C(C#N)N2C1=CC=CC=C1 OQRSWWCIZIRDKL-UHFFFAOYSA-N 0.000 claims description 2
- JISQYBYCOOTQNI-UHFFFAOYSA-N 1-(4-bromophenyl)-2-[3-fluoro-4-(trifluoromethyl)phenyl]-9-phenylpurin-6-one Chemical compound C1=C(C(F)(F)F)C(F)=CC(C=2N(C(=O)C=3N=CN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Br)=CC=2)=C1 JISQYBYCOOTQNI-UHFFFAOYSA-N 0.000 claims description 2
- HKRFOIAWIDPALW-UHFFFAOYSA-N 1-(4-bromophenyl)-8-ethyl-2-(4-ethylphenyl)-9-phenylpurin-6-one Chemical compound C=1C=CC=CC=1N1C(CC)=NC(C(N2C=3C=CC(Br)=CC=3)=O)=C1N=C2C1=CC=C(CC)C=C1 HKRFOIAWIDPALW-UHFFFAOYSA-N 0.000 claims description 2
- IBHGHBZOPWSKNB-UHFFFAOYSA-N 1-(4-bromophenyl)-8-ethyl-2-(4-methylphenyl)-9-phenylpurin-6-one Chemical compound C=1C=CC=CC=1N1C(CC)=NC(C(N2C=3C=CC(Br)=CC=3)=O)=C1N=C2C1=CC=C(C)C=C1 IBHGHBZOPWSKNB-UHFFFAOYSA-N 0.000 claims description 2
- QWMMPQKBYGZDSP-UHFFFAOYSA-N 1-(4-bromophenyl)-8-ethyl-9-phenyl-2-[4-(trichloromethyl)phenyl]purin-6-one Chemical compound C=1C=CC=CC=1N1C(CC)=NC(C(N2C=3C=CC(Br)=CC=3)=O)=C1N=C2C1=CC=C(C(Cl)(Cl)Cl)C=C1 QWMMPQKBYGZDSP-UHFFFAOYSA-N 0.000 claims description 2
- WTHBOWCNOUYZOA-UHFFFAOYSA-N 1-(4-bromophenyl)-8-methyl-9-phenyl-2-[4-(trifluoromethyl)phenyl]purin-6-one Chemical compound C=1C=CC=CC=1N1C(C)=NC(C(N2C=3C=CC(Br)=CC=3)=O)=C1N=C2C1=CC=C(C(F)(F)F)C=C1 WTHBOWCNOUYZOA-UHFFFAOYSA-N 0.000 claims description 2
- JWQLSSQYJCSNQE-UHFFFAOYSA-N 1-(4-bromophenyl)-9-phenyl-2-[2-(trifluoromethyl)phenyl]purin-6-one Chemical compound FC(F)(F)C1=CC=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 JWQLSSQYJCSNQE-UHFFFAOYSA-N 0.000 claims description 2
- OWHPKWMVOHOJQK-UHFFFAOYSA-N 1-(4-bromophenyl)-9-phenyl-2-[4-(trifluoromethyl)phenyl]purin-6-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 OWHPKWMVOHOJQK-UHFFFAOYSA-N 0.000 claims description 2
- JDVKBXIHSOCMAV-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dimethylphenyl)-9-phenylpurin-6-one Chemical compound CC1=CC(C)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 JDVKBXIHSOCMAV-UHFFFAOYSA-N 0.000 claims description 2
- PHLPZNWPHCEADL-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2-fluoro-4-methylphenyl)-9-phenylpurin-6-one Chemical compound FC1=CC(C)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 PHLPZNWPHCEADL-UHFFFAOYSA-N 0.000 claims description 2
- CZPBEGJZHWUKPZ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(4-cyclohexylphenyl)-9-phenylpurin-6-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(N=CN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(C2CCCCC2)C=C1 CZPBEGJZHWUKPZ-UHFFFAOYSA-N 0.000 claims description 2
- VGMGRGYTOHHSAI-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(4-cyclopropylphenyl)-9-phenylpurin-6-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(N=CN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(C2CC2)C=C1 VGMGRGYTOHHSAI-UHFFFAOYSA-N 0.000 claims description 2
- NPJFTKJUWYOJER-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(4-ethenylphenyl)-9-phenylpurin-6-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(N=CN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(C=C)C=C1 NPJFTKJUWYOJER-UHFFFAOYSA-N 0.000 claims description 2
- VQXTZDRJNSQUHQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(4-ethylphenyl)-9-phenylpurin-6-one Chemical compound C1=CC(CC)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 VQXTZDRJNSQUHQ-UHFFFAOYSA-N 0.000 claims description 2
- IKMJZMDXNBXBAO-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(4-hydroxyphenyl)-9-phenylpurin-6-one Chemical compound C1=CC(O)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 IKMJZMDXNBXBAO-UHFFFAOYSA-N 0.000 claims description 2
- AQTASVMWPMYTAR-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(4-methylphenyl)-9-phenylpurin-6-one Chemical compound C1=CC(C)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 AQTASVMWPMYTAR-UHFFFAOYSA-N 0.000 claims description 2
- KXMHLCFEFPTJCX-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(4-methylsulfonylphenyl)-9-phenylpurin-6-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 KXMHLCFEFPTJCX-UHFFFAOYSA-N 0.000 claims description 2
- CMDYERVPPMQQJM-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[2-fluoro-4-(trifluoromethyl)phenyl]-9-phenylpurin-6-one Chemical compound FC1=CC(C(F)(F)F)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 CMDYERVPPMQQJM-UHFFFAOYSA-N 0.000 claims description 2
- WNHYLOHEKJMOGU-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-(2-chloropyrimidin-4-yl)phenyl]-9-phenylpurin-6-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(N=CN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(C=2N=C(Cl)N=CC=2)C=C1 WNHYLOHEKJMOGU-UHFFFAOYSA-N 0.000 claims description 2
- BOXDPJIUMJCZMT-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-(2-fluorophenyl)phenyl]-9-phenylpurin-6-one Chemical compound FC1=CC=CC=C1C1=CC=C(C=2N(C(=O)C=3N=CN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C=C1 BOXDPJIUMJCZMT-UHFFFAOYSA-N 0.000 claims description 2
- LZWBZKQUNLIXRO-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-(2-methyl-1,2,4-triazol-3-yl)phenyl]-9-phenylpurin-6-one Chemical compound CN1N=CN=C1C1=CC=C(C=2N(C(=O)C=3N=CN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C=C1 LZWBZKQUNLIXRO-UHFFFAOYSA-N 0.000 claims description 2
- SJIRSUMVHGVTSH-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-(2-methylpropyl)phenyl]-9-phenylpurin-6-one Chemical compound C1=CC(CC(C)C)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 SJIRSUMVHGVTSH-UHFFFAOYSA-N 0.000 claims description 2
- MROOWUVAXBDEBA-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-(3-fluorophenyl)phenyl]-9-phenylpurin-6-one Chemical compound FC1=CC=CC(C=2C=CC(=CC=2)C=2N(C(=O)C=3N=CN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=C1 MROOWUVAXBDEBA-UHFFFAOYSA-N 0.000 claims description 2
- LSWYXPOSEUPUNV-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-(4-fluorophenyl)phenyl]-9-phenylpurin-6-one Chemical compound C1=CC(F)=CC=C1C1=CC=C(C=2N(C(=O)C=3N=CN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C=C1 LSWYXPOSEUPUNV-UHFFFAOYSA-N 0.000 claims description 2
- QYAXBQQYTZEMRY-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-(diethylaminomethyl)phenyl]-9-phenylpurin-6-one Chemical compound C1=CC(CN(CC)CC)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 QYAXBQQYTZEMRY-UHFFFAOYSA-N 0.000 claims description 2
- SSXVUQNBYOWXNP-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-(morpholin-4-ylmethyl)phenyl]-9-phenylpurin-6-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(N=CN2C=3C=CC=CC=3)=C2N=C1C(C=C1)=CC=C1CN1CCOCC1 SSXVUQNBYOWXNP-UHFFFAOYSA-N 0.000 claims description 2
- BZRROWGMXIIJNF-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-[(2-methylpropylamino)methyl]phenyl]-9-phenylpurin-6-one Chemical compound C1=CC(CNCC(C)C)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 BZRROWGMXIIJNF-UHFFFAOYSA-N 0.000 claims description 2
- COKBCNBCYPSBSO-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-[(cyclopropylmethylamino)methyl]phenyl]-9-phenylpurin-6-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(N=CN2C=3C=CC=CC=3)=C2N=C1C(C=C1)=CC=C1CNCC1CC1 COKBCNBCYPSBSO-UHFFFAOYSA-N 0.000 claims description 2
- ZRDOXHXOEKLHLM-UHFFFAOYSA-N 1-(4-chlorophenyl)-8-(dimethylamino)-9-phenyl-2-[4-(trifluoromethyl)phenyl]purin-6-one Chemical compound C=1C=CC=CC=1N1C(N(C)C)=NC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2C1=CC=C(C(F)(F)F)C=C1 ZRDOXHXOEKLHLM-UHFFFAOYSA-N 0.000 claims description 2
- BODVBOCQUXLMLO-UHFFFAOYSA-N 1-(4-chlorophenyl)-8-ethyl-9-phenyl-2-[4-(trifluoromethyl)phenyl]purin-6-one Chemical compound C=1C=CC=CC=1N1C(CC)=NC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2C1=CC=C(C(F)(F)F)C=C1 BODVBOCQUXLMLO-UHFFFAOYSA-N 0.000 claims description 2
- LSILAWNOINUOIN-UHFFFAOYSA-N 1-(4-chlorophenyl)-9-phenyl-2-(4-pyrazol-1-ylphenyl)purin-6-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(N=CN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(N2N=CC=C2)C=C1 LSILAWNOINUOIN-UHFFFAOYSA-N 0.000 claims description 2
- BHIFUCOXDGXAMK-UHFFFAOYSA-N 1-(4-chlorophenyl)-9-phenyl-2-(4-pyridin-3-ylphenyl)purin-6-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(N=CN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(C=2C=NC=CC=2)C=C1 BHIFUCOXDGXAMK-UHFFFAOYSA-N 0.000 claims description 2
- SBABBAPPDPTPIH-UHFFFAOYSA-N 1-(4-chlorophenyl)-9-phenyl-2-[4-(1h-1,2,4-triazol-5-yl)phenyl]purin-6-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(N=CN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(C=2NN=CN=2)C=C1 SBABBAPPDPTPIH-UHFFFAOYSA-N 0.000 claims description 2
- VEKGCUXNOUIBNQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-9-phenyl-2-[4-(propan-2-yloxymethyl)phenyl]purin-6-one Chemical compound C1=CC(COC(C)C)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 VEKGCUXNOUIBNQ-UHFFFAOYSA-N 0.000 claims description 2
- FBDYQWZZSYFJRW-UHFFFAOYSA-N 1-(4-chlorophenyl)-9-phenyl-2-[4-(trifluoromethyl)phenyl]purin-6-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 FBDYQWZZSYFJRW-UHFFFAOYSA-N 0.000 claims description 2
- AUFHOPBIGBWDCS-UHFFFAOYSA-N 2-(4-bromophenyl)-1-(4-chlorophenyl)-9-phenylpurin-6-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(N=CN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(Br)C=C1 AUFHOPBIGBWDCS-UHFFFAOYSA-N 0.000 claims description 2
- ZKGOTJDYYKPBAV-UHFFFAOYSA-N 2-(4-butoxyphenyl)-1-(4-chlorophenyl)-9-phenylpurin-6-one Chemical compound C1=CC(OCCCC)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 ZKGOTJDYYKPBAV-UHFFFAOYSA-N 0.000 claims description 2
- UESYWYKKRUYZFE-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenyl)-1-(4-chlorophenyl)-9-phenylpurin-6-one Chemical compound FC1=CC(Cl)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 UESYWYKKRUYZFE-UHFFFAOYSA-N 0.000 claims description 2
- WBOQBXAJVGODIT-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(2-fluorophenyl)-7-phenylpurin-6-one Chemical compound FC1=CC=CC=C1N1C(=O)C(N(C=2C=CC=CC=2)C=N2)=C2N=C1C1=CC=C(Cl)C=C1 WBOQBXAJVGODIT-UHFFFAOYSA-N 0.000 claims description 2
- LVJSAYGXAGEWQL-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(4-methylphenyl)-7-phenylpurin-6-one Chemical compound C1=CC(C)=CC=C1N1C(=O)C(N(C=2C=CC=CC=2)C=N2)=C2N=C1C1=CC=C(Cl)C=C1 LVJSAYGXAGEWQL-UHFFFAOYSA-N 0.000 claims description 2
- UGQBRSYOCBLADL-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-[4-(2-fluorophenyl)phenyl]-7-phenylpurin-6-one Chemical compound FC1=CC=CC=C1C1=CC=C(N2C(C=3N(C=4C=CC=CC=4)C=NC=3N=C2C=2C=CC(Cl)=CC=2)=O)C=C1 UGQBRSYOCBLADL-UHFFFAOYSA-N 0.000 claims description 2
- GFBVBTPWGMKIQJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-[4-(3-fluorophenyl)phenyl]-7-phenylpurin-6-one Chemical compound FC1=CC=CC(C=2C=CC(=CC=2)N2C(C=3N(C=4C=CC=CC=4)C=NC=3N=C2C=2C=CC(Cl)=CC=2)=O)=C1 GFBVBTPWGMKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- HXORJXWSXRVNIH-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-[4-(4-fluorophenyl)phenyl]-7-phenylpurin-6-one Chemical compound C1=CC(F)=CC=C1C1=CC=C(N2C(C=3N(C=4C=CC=CC=4)C=NC=3N=C2C=2C=CC(Cl)=CC=2)=O)C=C1 HXORJXWSXRVNIH-UHFFFAOYSA-N 0.000 claims description 2
- RUSFGTZYRAYLLD-UHFFFAOYSA-N 2-[4-(chloromethyl)phenyl]-1-(4-chlorophenyl)-9-phenylpurin-6-one Chemical compound C1=CC(CCl)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 RUSFGTZYRAYLLD-UHFFFAOYSA-N 0.000 claims description 2
- TZBKUSCZXKRNHN-UHFFFAOYSA-N 3-[1-(4-bromophenyl)-2-(4-methylphenyl)-6-oxopurin-9-yl]benzonitrile Chemical compound C1=CC(C)=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1N=CN2C1=CC=CC(C#N)=C1 TZBKUSCZXKRNHN-UHFFFAOYSA-N 0.000 claims description 2
- BNFMAWGNJLMYEG-UHFFFAOYSA-N 4-[1-(4-chlorophenyl)-6-oxo-9-phenylpurin-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=CN2C1=CC=CC=C1 BNFMAWGNJLMYEG-UHFFFAOYSA-N 0.000 claims description 2
- QFIVFINKWOVMNI-UHFFFAOYSA-N 4-[5-(4-bromophenyl)-6-(2-fluorophenyl)-4-oxopyrazolo[3,4-d]pyrimidin-1-yl]benzonitrile Chemical compound FC1=CC=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1C=NN2C1=CC=C(C#N)C=C1 QFIVFINKWOVMNI-UHFFFAOYSA-N 0.000 claims description 2
- JDDVRJUYXRYOMX-UHFFFAOYSA-N 4-[6-(2-fluorophenyl)-4-oxo-1-phenylpyrazolo[3,4-d]pyrimidin-5-yl]benzonitrile Chemical compound FC1=CC=CC=C1C(N(C1=O)C=2C=CC(=CC=2)C#N)=NC2=C1C=NN2C1=CC=CC=C1 JDDVRJUYXRYOMX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- IKAKSZRLDRHKKV-UHFFFAOYSA-N 5-(4-bromophenyl)-1-cyclohexyl-6-(2-fluorophenyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1C=NN2C1CCCCC1 IKAKSZRLDRHKKV-UHFFFAOYSA-N 0.000 claims description 2
- VMEPLDPNGMZKAK-UHFFFAOYSA-N 5-(4-bromophenyl)-1-phenyl-6-(4-phenylpiperazin-1-yl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Br)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1N1CCN(C=2C=CC=CC=2)CC1 VMEPLDPNGMZKAK-UHFFFAOYSA-N 0.000 claims description 2
- HJNRDAPPYFBISY-UHFFFAOYSA-N 5-(4-bromophenyl)-1-phenyl-6-[2-(trifluoromethyl)phenyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC(F)(F)C1=CC=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 HJNRDAPPYFBISY-UHFFFAOYSA-N 0.000 claims description 2
- NLGYFLWYGHTFDA-UHFFFAOYSA-N 5-(4-bromophenyl)-1-phenyl-6-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 NLGYFLWYGHTFDA-UHFFFAOYSA-N 0.000 claims description 2
- RJSHELDJUSGJSA-UHFFFAOYSA-N 5-(4-bromophenyl)-1-phenyl-6-[4-(trifluoromethyl)phenyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 RJSHELDJUSGJSA-UHFFFAOYSA-N 0.000 claims description 2
- UUPNPRGFKWHLKH-UHFFFAOYSA-N 5-(4-bromophenyl)-1-phenyl-6-pyridin-3-ylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Br)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=CN=C1 UUPNPRGFKWHLKH-UHFFFAOYSA-N 0.000 claims description 2
- FOUGBFGIJMJMHB-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(2-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound ClC1=CC=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 FOUGBFGIJMJMHB-UHFFFAOYSA-N 0.000 claims description 2
- LTNPJQLFYHCNGF-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(2-fluorophenyl)-1-(2-hydroxyethyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound OCCN1N=CC(C(N2C=3C=CC(Br)=CC=3)=O)=C1N=C2C1=CC=CC=C1F LTNPJQLFYHCNGF-UHFFFAOYSA-N 0.000 claims description 2
- VDWIKOJRKBDQEE-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(2-fluorophenyl)-1-(3-fluorophenyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC(N2C3=C(C(N(C=4C=CC(Br)=CC=4)C(C=4C(=CC=CC=4)F)=N3)=O)C=N2)=C1 VDWIKOJRKBDQEE-UHFFFAOYSA-N 0.000 claims description 2
- JZWNLPCLDXNWAP-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(2-fluorophenyl)-1-[4-(trifluoromethyl)phenyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1C=NN2C1=CC=C(C(F)(F)F)C=C1 JZWNLPCLDXNWAP-UHFFFAOYSA-N 0.000 claims description 2
- NOJXMOVYUPTUNN-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(2-fluorophenyl)-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1C=NN2 NOJXMOVYUPTUNN-UHFFFAOYSA-N 0.000 claims description 2
- WXGNKFJLXNBNME-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(2-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 WXGNKFJLXNBNME-UHFFFAOYSA-N 0.000 claims description 2
- JZTNHBLCQUUIJA-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(3-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound ClC1=CC=CC(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Br)=CC=2)=C1 JZTNHBLCQUUIJA-UHFFFAOYSA-N 0.000 claims description 2
- MIWBSZXTENKDNP-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(3-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Br)=CC=2)=C1 MIWBSZXTENKDNP-UHFFFAOYSA-N 0.000 claims description 2
- WIUCPYCEYTYWDM-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(4-chlorophenyl)-1-methyl-3-phenylpyrazolo[4,3-d]pyrimidin-7-one Chemical class C1=2N=C(C=3C=CC(Br)=CC=3)N(C=3C=CC(Cl)=CC=3)C(=O)C=2N(C)N=C1C1=CC=CC=C1 WIUCPYCEYTYWDM-UHFFFAOYSA-N 0.000 claims description 2
- SGGJKJSDGNSNJN-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(4-chlorophenyl)-1-methylsulfonyl-3-phenylpyrazolo[4,3-d]pyrimidin-7-one Chemical class C1=2N=C(C=3C=CC(Br)=CC=3)N(C=3C=CC(Cl)=CC=3)C(=O)C=2N(S(=O)(=O)C)N=C1C1=CC=CC=C1 SGGJKJSDGNSNJN-UHFFFAOYSA-N 0.000 claims description 2
- DRMHLXRMPCRKLA-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(4-chlorophenyl)-3-phenyl-1h-pyrazolo[4,3-d]pyrimidin-7-one Chemical class C1=CC(Cl)=CC=C1N1C(=O)C(NN=C2C=3C=CC=CC=3)=C2N=C1C1=CC=C(Br)C=C1 DRMHLXRMPCRKLA-UHFFFAOYSA-N 0.000 claims description 2
- GVCQZIWKXNNQLH-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(4-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 GVCQZIWKXNNQLH-UHFFFAOYSA-N 0.000 claims description 2
- MGNLIZFEFJJQPJ-UHFFFAOYSA-N 5-(4-bromophenyl)-6-[4-(4-fluorophenyl)piperazin-1-yl]-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1N1CCN(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Br)=CC=2)CC1 MGNLIZFEFJJQPJ-UHFFFAOYSA-N 0.000 claims description 2
- JCBYGXZQZIBSJB-UHFFFAOYSA-N 5-(4-butoxyphenyl)-6-(2-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(OCCCC)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=CC=C1F JCBYGXZQZIBSJB-UHFFFAOYSA-N 0.000 claims description 2
- JYRKWNNWEOGAEQ-UHFFFAOYSA-N 5-(4-chloro-2-fluorophenyl)-6-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC(Cl)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(Cl)C=C1 JYRKWNNWEOGAEQ-UHFFFAOYSA-N 0.000 claims description 2
- PIQOWPRRCULDDD-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-phenyl-6-(4-pyrazol-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(N2N=CC=C2)C=C1 PIQOWPRRCULDDD-UHFFFAOYSA-N 0.000 claims description 2
- PHUDPJVYKAMFLB-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-phenyl-6-(4-pyridin-3-ylphenyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(C=2C=NC=CC=2)C=C1 PHUDPJVYKAMFLB-UHFFFAOYSA-N 0.000 claims description 2
- KGFQWMXEDVCLOH-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-phenyl-6-(4-pyridin-4-ylpiperazin-1-yl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1N1CCN(C=2C=CN=CC=2)CC1 KGFQWMXEDVCLOH-UHFFFAOYSA-N 0.000 claims description 2
- MSMRRMVLQSMLAF-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-phenyl-6-(4-thiophen-3-ylphenyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(C2=CSC=C2)C=C1 MSMRRMVLQSMLAF-UHFFFAOYSA-N 0.000 claims description 2
- ZIVDTPSEPAUQHH-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-phenyl-6-[4-(trifluoromethyl)phenyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 ZIVDTPSEPAUQHH-UHFFFAOYSA-N 0.000 claims description 2
- MEDKQSKIMGKDJT-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-phenyl-6-[4-[4-(trifluoromethyl)phenyl]phenyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C=C1 MEDKQSKIMGKDJT-UHFFFAOYSA-N 0.000 claims description 2
- BYYPHJDVWJEWNI-UHFFFAOYSA-N 5-(4-chlorophenyl)-3-methylsulfonyl-1-phenyl-6-(4-pyridin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=2N=C(C=3C=CC(=CC=3)C=3C=CN=CC=3)N(C=3C=CC(Cl)=CC=3)C(=O)C=2C(S(=O)(=O)C)=NN1C1=CC=CC=C1 BYYPHJDVWJEWNI-UHFFFAOYSA-N 0.000 claims description 2
- KKHWJDKTKHQREG-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2-chloro-4-phenylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(C=2C=CC=CC=2)C=C1Cl KKHWJDKTKHQREG-UHFFFAOYSA-N 0.000 claims description 2
- QCBWYURTADFEAI-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2-fluoro-4-phenylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC(C=2C=CC=CC=2)=CC=C1C1=NC=2N(C=3C=CC=CC=3)N=CC=2C(=O)N1C1=CC=C(Cl)C=C1 QCBWYURTADFEAI-UHFFFAOYSA-N 0.000 claims description 2
- GWLCQLWCXFVIMX-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2-methylphenoxy)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC=C1OC(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 GWLCQLWCXFVIMX-UHFFFAOYSA-N 0.000 claims description 2
- IMHKZEZJRDGBQK-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(3-fluoro-4-phenylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=CC=C1C1=CC=CC=C1 IMHKZEZJRDGBQK-UHFFFAOYSA-N 0.000 claims description 2
- GIOHKSNBXOHGOF-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(4-methylsulfonylpiperazin-1-yl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1CN(S(=O)(=O)C)CCN1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 GIOHKSNBXOHGOF-UHFFFAOYSA-N 0.000 claims description 2
- HGYQQWPCMZSXKF-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-[2-fluoro-4-(4-methylpiperazin-1-yl)phenyl]-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CC=C(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C(F)=C1 HGYQQWPCMZSXKF-UHFFFAOYSA-N 0.000 claims description 2
- HPFPVYXUWCFISM-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-[3-fluoro-4-(4-methylpiperazin-1-yl)phenyl]-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CC=C(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C=C1F HPFPVYXUWCFISM-UHFFFAOYSA-N 0.000 claims description 2
- SJTMDYPARQJDJF-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-[4-(2-fluorophenyl)phenyl]-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC=C1C1=CC=C(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C=C1 SJTMDYPARQJDJF-UHFFFAOYSA-N 0.000 claims description 2
- GCGNQBACGHELRT-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-[4-(2-methylphenyl)phenyl]-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC=C1C1=CC=C(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C=C1 GCGNQBACGHELRT-UHFFFAOYSA-N 0.000 claims description 2
- ZYWUCANBKHJQRE-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-[4-(2-methylpyrazol-3-yl)phenyl]-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CN1N=CC=C1C1=CC=C(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C=C1 ZYWUCANBKHJQRE-UHFFFAOYSA-N 0.000 claims description 2
- VMDLPPCXABZQFN-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-[4-(2-methylpyrimidin-4-yl)phenyl]-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=NC=CC(C=2C=CC(=CC=2)C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=N1 VMDLPPCXABZQFN-UHFFFAOYSA-N 0.000 claims description 2
- UOXJPNOQIXYJJC-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-[4-(3,6-dimethylpyrazin-2-yl)phenyl]-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CN=C(C)C(C=2C=CC(=CC=2)C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=N1 UOXJPNOQIXYJJC-UHFFFAOYSA-N 0.000 claims description 2
- MHNFDYWJCGTNOT-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-[4-(3-methylphenyl)phenyl]-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC(C=2C=CC(=CC=2)C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=C1 MHNFDYWJCGTNOT-UHFFFAOYSA-N 0.000 claims description 2
- BJEHPWCUHIWNIP-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-[4-(4-fluorophenyl)phenyl]-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1C1=CC=C(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C=C1 BJEHPWCUHIWNIP-UHFFFAOYSA-N 0.000 claims description 2
- VMOLNJHNXPRHRC-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-[4-(4-fluorophenyl)piperazin-1-yl]-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1N1CCN(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)CC1 VMOLNJHNXPRHRC-UHFFFAOYSA-N 0.000 claims description 2
- BRHNZXQWAUITHV-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-[4-(4-methylphenyl)phenyl]-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C)=CC=C1C1=CC=C(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C=C1 BRHNZXQWAUITHV-UHFFFAOYSA-N 0.000 claims description 2
- ATNOSWWIMUJTHM-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-[4-(4-methylpiperazin-1-yl)phenyl]-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CC=C(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C=C1 ATNOSWWIMUJTHM-UHFFFAOYSA-N 0.000 claims description 2
- MNDHYKAEBQEDNV-UHFFFAOYSA-N 5-benzyl-6-(2-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC=C1C(N(C1=O)CC=2C=CC=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 MNDHYKAEBQEDNV-UHFFFAOYSA-N 0.000 claims description 2
- IJIMFLXQXAUTDI-UHFFFAOYSA-N 5-cyclohexyl-6-(2-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC=C1C(N(C1=O)C2CCCCC2)=NC2=C1C=NN2C1=CC=CC=C1 IJIMFLXQXAUTDI-UHFFFAOYSA-N 0.000 claims description 2
- YTKYNXCSIAETLJ-UHFFFAOYSA-N 6-(2-bromophenyl)-5-(4-bromophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Br)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=CC=C1Br YTKYNXCSIAETLJ-UHFFFAOYSA-N 0.000 claims description 2
- YNGOZJVXBUBNBW-UHFFFAOYSA-N 6-(2-fluorophenyl)-1-phenyl-5-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC=C1C(N(C1=O)C=2C=CC(OC(F)(F)F)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 YNGOZJVXBUBNBW-UHFFFAOYSA-N 0.000 claims description 2
- LTFVTABCNKTQEV-UHFFFAOYSA-N 6-(2-fluorophenyl)-1-phenyl-5-[4-(trifluoromethyl)phenyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC=C1C(N(C1=O)C=2C=CC(=CC=2)C(F)(F)F)=NC2=C1C=NN2C1=CC=CC=C1 LTFVTABCNKTQEV-UHFFFAOYSA-N 0.000 claims description 2
- RSPGDBGQPHGGOB-UHFFFAOYSA-N 6-(2-fluorophenyl)-1-phenyl-5-pyridin-3-ylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC=C1C(N(C1=O)C=2C=NC=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 RSPGDBGQPHGGOB-UHFFFAOYSA-N 0.000 claims description 2
- HCTLUSPPKSGJDR-UHFFFAOYSA-N 6-(4-bromo-2-chlorophenyl)-5-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(Br)C=C1Cl HCTLUSPPKSGJDR-UHFFFAOYSA-N 0.000 claims description 2
- WIRXLXSPIKMAHZ-UHFFFAOYSA-N 6-(4-bromo-2-fluorophenyl)-5-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC(Br)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 WIRXLXSPIKMAHZ-UHFFFAOYSA-N 0.000 claims description 2
- MPCMKOWKYVILRR-UHFFFAOYSA-N 6-(4-bromo-3-fluorophenyl)-5-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=C(Br)C(F)=CC(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=C1 MPCMKOWKYVILRR-UHFFFAOYSA-N 0.000 claims description 2
- GZLNDAPAIUIDQU-UHFFFAOYSA-N 6-(4-bromophenyl)-5-(4-chlorophenyl)-3-(morpholine-4-carbonyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C(C(=O)N2CCOCC2)=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(Br)C=C1 GZLNDAPAIUIDQU-UHFFFAOYSA-N 0.000 claims description 2
- VVSOPFHEBCYHKN-UHFFFAOYSA-N 6-[2-chloro-4-(4-methylpiperazin-1-yl)phenyl]-5-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CC=C(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C(Cl)=C1 VVSOPFHEBCYHKN-UHFFFAOYSA-N 0.000 claims description 2
- MQPMOVJMBCYFOH-UHFFFAOYSA-N 6-[4-(2-butoxyethenyl)phenyl]-5-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C=COCCCC)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 MQPMOVJMBCYFOH-UHFFFAOYSA-N 0.000 claims description 2
- DXXRAYGXYSZEGY-UHFFFAOYSA-N 6-[4-(6-aminopyridin-2-yl)phenyl]-5-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound NC1=CC=CC(C=2C=CC(=CC=2)C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=N1 DXXRAYGXYSZEGY-UHFFFAOYSA-N 0.000 claims description 2
- VJPMWWNCNBLURA-UHFFFAOYSA-N 8-bromo-1-(4-bromophenyl)-2-(4-methylphenyl)-9-phenylpurin-6-one Chemical compound C1=CC(C)=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1N=C(Br)N2C1=CC=CC=C1 VJPMWWNCNBLURA-UHFFFAOYSA-N 0.000 claims description 2
- JEKFZGFWTFBSGB-UHFFFAOYSA-N 8-bromo-2-(4-bromophenyl)-1-(4-chlorophenyl)-9-phenylpurin-6-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(N=C(Br)N2C=3C=CC=CC=3)=C2N=C1C1=CC=C(Br)C=C1 JEKFZGFWTFBSGB-UHFFFAOYSA-N 0.000 claims description 2
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 2
- RQVLVUDGCBVBKP-UHFFFAOYSA-N BrC1=CC=C(C=C1)C=1C=C(CC(C(=O)O)(C1C1=C(C=CC=C1)F)C)C(=O)O Chemical compound BrC1=CC=C(C=C1)C=1C=C(CC(C(=O)O)(C1C1=C(C=CC=C1)F)C)C(=O)O RQVLVUDGCBVBKP-UHFFFAOYSA-N 0.000 claims description 2
- SDUMHEKPEVLBKM-UHFFFAOYSA-N C(CCC)N1N=CC2=C1N=C(NC2=O)C2=C(C=CC=C2)F Chemical group C(CCC)N1N=CC2=C1N=C(NC2=O)C2=C(C=CC=C2)F SDUMHEKPEVLBKM-UHFFFAOYSA-N 0.000 claims description 2
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 2
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims description 2
- 208000006029 Cardiomegaly Diseases 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 206010012289 Dementia Diseases 0.000 claims description 2
- 206010012442 Dermatitis contact Diseases 0.000 claims description 2
- 208000012661 Dyskinesia Diseases 0.000 claims description 2
- 206010014612 Encephalitis viral Diseases 0.000 claims description 2
- 208000009329 Graft vs Host Disease Diseases 0.000 claims description 2
- 208000001204 Hashimoto Disease Diseases 0.000 claims description 2
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims description 2
- 206010019280 Heart failures Diseases 0.000 claims description 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 206010022489 Insulin Resistance Diseases 0.000 claims description 2
- 206010026749 Mania Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 206010063837 Reperfusion injury Diseases 0.000 claims description 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 2
- 206010052779 Transplant rejections Diseases 0.000 claims description 2
- 201000010105 allergic rhinitis Diseases 0.000 claims description 2
- 230000002052 anaphylactic effect Effects 0.000 claims description 2
- 230000036506 anxiety Effects 0.000 claims description 2
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 230000000747 cardiac effect Effects 0.000 claims description 2
- 230000002490 cerebral effect Effects 0.000 claims description 2
- 208000010247 contact dermatitis Diseases 0.000 claims description 2
- 201000005577 familial hyperlipidemia Diseases 0.000 claims description 2
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 2
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- 208000037906 ischaemic injury Diseases 0.000 claims description 2
- 230000000302 ischemic effect Effects 0.000 claims description 2
- 206010025135 lupus erythematosus Diseases 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 2
- 208000020016 psychiatric disease Diseases 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 230000006403 short-term memory Effects 0.000 claims description 2
- WTVSOESDARPVQO-UHFFFAOYSA-N triazolo[4,5-d]pyrimidin-7-one Chemical class O=C1N=CN=C2N=NN=C12 WTVSOESDARPVQO-UHFFFAOYSA-N 0.000 claims description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 2
- 208000019553 vascular disease Diseases 0.000 claims description 2
- 201000002498 viral encephalitis Diseases 0.000 claims description 2
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 claims 1
- 229940126086 compound 21 Drugs 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 8
- 208000035475 disorder Diseases 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 85
- 239000000243 solution Substances 0.000 description 77
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 58
- 238000005160 1H NMR spectroscopy Methods 0.000 description 55
- 235000019439 ethyl acetate Nutrition 0.000 description 52
- 239000011541 reaction mixture Substances 0.000 description 52
- 239000002585 base Substances 0.000 description 51
- 238000006243 chemical reaction Methods 0.000 description 46
- 238000002360 preparation method Methods 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 29
- 238000003756 stirring Methods 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- 238000012360 testing method Methods 0.000 description 25
- 239000003795 chemical substances by application Substances 0.000 description 24
- 0 *C(C(C1=*)=C([N+]*)N=C(*)N1I)=N Chemical compound *C(C(C1=*)=C([N+]*)N=C(*)N1I)=N 0.000 description 23
- 238000005481 NMR spectroscopy Methods 0.000 description 23
- 239000012141 concentrate Substances 0.000 description 22
- 238000005406 washing Methods 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000007864 aqueous solution Substances 0.000 description 20
- 239000012044 organic layer Substances 0.000 description 20
- 238000000746 purification Methods 0.000 description 20
- 238000000605 extraction Methods 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
- 239000003153 chemical reaction reagent Substances 0.000 description 17
- 239000012043 crude product Substances 0.000 description 17
- 229960001866 silicon dioxide Drugs 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 238000003818 flash chromatography Methods 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000000284 extract Substances 0.000 description 13
- 238000001914 filtration Methods 0.000 description 13
- 241000699666 Mus <mouse, genus> Species 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 238000012545 processing Methods 0.000 description 10
- 239000012265 solid product Substances 0.000 description 10
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 208000024891 symptom Diseases 0.000 description 8
- 239000005557 antagonist Substances 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 238000003810 ethyl acetate extraction Methods 0.000 description 7
- 238000012746 preparative thin layer chromatography Methods 0.000 description 7
- 238000010926 purge Methods 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 230000003750 conditioning effect Effects 0.000 description 6
- 238000002386 leaching Methods 0.000 description 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 6
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 5
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 5
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 241001597008 Nomeidae Species 0.000 description 5
- 239000000556 agonist Substances 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 208000019425 cirrhosis of liver Diseases 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 235000012631 food intake Nutrition 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 230000007170 pathology Effects 0.000 description 5
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 5
- 229940002612 prodrug Drugs 0.000 description 5
- 239000000651 prodrug Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- 229910014265 BrCl Inorganic materials 0.000 description 4
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 description 4
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 150000001204 N-oxides Chemical class 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- JYVXNLLUYHCIIH-ZCFIWIBFSA-N R-mevalonolactone, (-)- Chemical class C[C@@]1(O)CCOC(=O)C1 JYVXNLLUYHCIIH-ZCFIWIBFSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 235000009120 camo Nutrition 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 235000005607 chanvre indien Nutrition 0.000 description 4
- 238000013016 damping Methods 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 231100000673 dose–response relationship Toxicity 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 238000011010 flushing procedure Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000011487 hemp Substances 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000004007 reversed phase HPLC Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 3
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010010774 Constipation Diseases 0.000 description 3
- 102400000322 Glucagon-like peptide 1 Human genes 0.000 description 3
- 101800000224 Glucagon-like peptide 1 Proteins 0.000 description 3
- 239000007995 HEPES buffer Substances 0.000 description 3
- 102000004877 Insulin Human genes 0.000 description 3
- 108090001061 Insulin Proteins 0.000 description 3
- 108090000028 Neprilysin Proteins 0.000 description 3
- 102000003729 Neprilysin Human genes 0.000 description 3
- 208000001132 Osteoporosis Diseases 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 150000001263 acyl chlorides Chemical class 0.000 description 3
- 229940025084 amphetamine Drugs 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 208000014797 chronic intestinal pseudoobstruction Diseases 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 210000004379 membrane Anatomy 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229960003562 phentermine Drugs 0.000 description 3
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 3
- 229940067157 phenylhydrazine Drugs 0.000 description 3
- 239000013641 positive control Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 230000005586 smoking cessation Effects 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 3
- XOFLBQFBSOEHOG-UUOKFMHZSA-N γS-GTP Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=S)[C@@H](O)[C@H]1O XOFLBQFBSOEHOG-UUOKFMHZSA-N 0.000 description 3
- JYVXNLLUYHCIIH-UHFFFAOYSA-N (+/-)-mevalonolactone Natural products CC1(O)CCOC(=O)C1 JYVXNLLUYHCIIH-UHFFFAOYSA-N 0.000 description 2
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- DLNKOYKMWOXYQA-CBAPKCEASA-N (-)-norephedrine Chemical compound C[C@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-CBAPKCEASA-N 0.000 description 2
- CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 description 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- IRSVDHPYXFLLDS-UHFFFAOYSA-N 2,4-dichloro-1-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1Cl IRSVDHPYXFLLDS-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- QHCVEFDYHZPJQU-UHFFFAOYSA-N 4-(2-oxo-1h-pyrimidin-6-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=NC(O)=N1 QHCVEFDYHZPJQU-UHFFFAOYSA-N 0.000 description 2
- YIMVMANWOQEKLD-UHFFFAOYSA-N 4-bromo-n-(4-chlorophenyl)benzenecarboximidoyl chloride Chemical compound C=1C=C(Br)C=CC=1C(Cl)=NC1=CC=C(Cl)C=C1 YIMVMANWOQEKLD-UHFFFAOYSA-N 0.000 description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 2
- SWVKFORRAJEMKK-UHFFFAOYSA-N 4-methylcyclohexane-1,1-diamine Chemical compound CC1CCC(N)(N)CC1 SWVKFORRAJEMKK-UHFFFAOYSA-N 0.000 description 2
- AENVNGDHIIEYHT-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(2-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 AENVNGDHIIEYHT-UHFFFAOYSA-N 0.000 description 2
- RRWFWCDDKDDOPI-UHFFFAOYSA-N 6-chloro-5-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1Cl RRWFWCDDKDDOPI-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 description 2
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 108010018763 Biotin carboxylase Proteins 0.000 description 2
- 102000004219 Brain-derived neurotrophic factor Human genes 0.000 description 2
- 108090000715 Brain-derived neurotrophic factor Proteins 0.000 description 2
- 239000004072 C09CA03 - Valsartan Substances 0.000 description 2
- 241000375384 Cannaboides Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
- 108010005939 Ciliary Neurotrophic Factor Proteins 0.000 description 2
- 102100031614 Ciliary neurotrophic factor Human genes 0.000 description 2
- 102100021752 Corticoliberin Human genes 0.000 description 2
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 2
- XXGMIHXASFDFSM-UHFFFAOYSA-N Delta9-tetrahydrocannabinol Natural products CCCCCc1cc2OC(C)(C)C3CCC(=CC3c2c(O)c1O)C XXGMIHXASFDFSM-UHFFFAOYSA-N 0.000 description 2
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 description 2
- 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 description 2
- VYLOWJQRXNQFLQ-UHFFFAOYSA-N FC1=C(C=CC=C1)C=1NC(C2=C(N1)NN=C2)=O Chemical compound FC1=C(C=CC=C1)C=1NC(C2=C(N1)NN=C2)=O VYLOWJQRXNQFLQ-UHFFFAOYSA-N 0.000 description 2
- 102000001267 GSK3 Human genes 0.000 description 2
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 102000016267 Leptin Human genes 0.000 description 2
- 108010092277 Leptin Proteins 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- ZPXSCAKFGYXMGA-UHFFFAOYSA-N Mazindol Chemical compound N12CCN=C2C2=CC=CC=C2C1(O)C1=CC=C(Cl)C=C1 ZPXSCAKFGYXMGA-UHFFFAOYSA-N 0.000 description 2
- 102000029828 Melanin-concentrating hormone receptor Human genes 0.000 description 2
- 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 description 2
- 102000004378 Melanocortin Receptors Human genes 0.000 description 2
- 108090000950 Melanocortin Receptors Proteins 0.000 description 2
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- LQACMNDSYOABHJ-UHFFFAOYSA-N N=C(C1=CC=CC=C1)ClCl Chemical compound N=C(C1=CC=CC=C1)ClCl LQACMNDSYOABHJ-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 108010015847 Non-Receptor Type 1 Protein Tyrosine Phosphatase Proteins 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 206010043903 Tobacco abuse Diseases 0.000 description 2
- KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical compound C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 description 2
- 102100033001 Tyrosine-protein phosphatase non-receptor type 1 Human genes 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229940077737 brain-derived neurotrophic factor Drugs 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 2
- 230000002354 daily effect Effects 0.000 description 2
- 229960005215 dichloroacetic acid Drugs 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- XXEPPPIWZFICOJ-UHFFFAOYSA-N diethylpropion Chemical compound CCN(CC)C(C)C(=O)C1=CC=CC=C1 XXEPPPIWZFICOJ-UHFFFAOYSA-N 0.000 description 2
- 229960004890 diethylpropion Drugs 0.000 description 2
- 229960005156 digoxin Drugs 0.000 description 2
- MOAVUYWYFFCBNM-PUGKRICDSA-N digoxin(1-) Chemical compound C[C@H]([C@H]([C@H](C1)O)O)O[C@H]1O[C@H]([C@@H](C)O[C@H](C1)O[C@H]([C@@H](C)O[C@H](C2)O[C@@H](CC3)C[C@@H](CC4)[C@@]3(C)[C@@H](C[C@H]([C@]3(C)[C@H](CC5)C([CH-]O6)=CC6=O)O)[C@@H]4[C@]35O)[C@H]2O)[C@H]1O MOAVUYWYFFCBNM-PUGKRICDSA-N 0.000 description 2
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229960002464 fluoxetine Drugs 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000002631 hypothermal effect Effects 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 2
- 229940039781 leptin Drugs 0.000 description 2
- 102000004311 liver X receptors Human genes 0.000 description 2
- 108090000865 liver X receptors Proteins 0.000 description 2
- 229960004844 lovastatin Drugs 0.000 description 2
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 2
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 2
- 229960000299 mazindol Drugs 0.000 description 2
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 2
- 229940057061 mevalonolactone Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- LICDSLAPJLYBPE-UHFFFAOYSA-N n'-(4-bromophenyl)-2-fluorobenzenecarboximidamide Chemical compound FC1=CC=CC=C1C(=N)NC1=CC=C(Br)C=C1 LICDSLAPJLYBPE-UHFFFAOYSA-N 0.000 description 2
- AEXITZJSLGALNH-UHFFFAOYSA-N n'-hydroxyethanimidamide Chemical compound CC(N)=NO AEXITZJSLGALNH-UHFFFAOYSA-N 0.000 description 2
- LDZAMVJRGBUYEO-UHFFFAOYSA-N n-(4-bromophenyl)-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC1=CC=C(Br)C=C1 LDZAMVJRGBUYEO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000001537 neural effect Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound 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 description 2
- 229960001243 orlistat Drugs 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- UFZNZKGKBWOSJG-UHFFFAOYSA-N purin-2-one Chemical class O=C1N=CC2=NC=NC2=N1 UFZNZKGKBWOSJG-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 239000002287 radioligand Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000003345 scintillation counting Methods 0.000 description 2
- 229960004425 sibutramine Drugs 0.000 description 2
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 2
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229910000080 stannane Inorganic materials 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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
- 230000000699 topical effect Effects 0.000 description 2
- 229960004394 topiramate Drugs 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 229960004699 valsartan Drugs 0.000 description 2
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 229960001254 vildagliptin Drugs 0.000 description 2
- 229940009065 wellbutrin Drugs 0.000 description 2
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 1
- MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 description 1
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 1
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 1
- BOOOLEGQBVUTKC-NVQSDHBMSA-N (2e,4e)-3-methyl-5-[(1s,2s)-2-methyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)cyclopropyl]penta-2,4-dienoic acid Chemical compound OC(=O)\C=C(/C)\C=C\[C@@H]1C[C@]1(C)C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 BOOOLEGQBVUTKC-NVQSDHBMSA-N 0.000 description 1
- FONCZICQWCUXEB-RUZDIDTESA-N (2r)-2-[4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-2,6-dimethylphenoxy]-3-phenylpropanoic acid Chemical compound C([C@@H](OC1=C(C)C=C(C=C1C)C=1C2=CC=CC=C2C(Br)=C2SC(=C(C2=1)C)C)C(O)=O)C1=CC=CC=C1 FONCZICQWCUXEB-RUZDIDTESA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- LPUDGHQMOAHMMF-JBACZVJFSA-N (2s)-2-[[[(2s)-6-amino-2-(methanesulfonamido)hexanoyl]amino]methyl]-3-[1-[[(1s)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl]cyclopentyl]propanoic acid Chemical compound N([C@@H](CC=1C=CC(O)=CC=1)C(O)=O)C(=O)C1(C[C@@H](CNC(=O)[C@H](CCCCN)NS(=O)(=O)C)C(O)=O)CCCC1 LPUDGHQMOAHMMF-JBACZVJFSA-N 0.000 description 1
- BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 description 1
- KNXQDJCZSVHEIW-UHFFFAOYSA-N (3-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(F)=C1 KNXQDJCZSVHEIW-UHFFFAOYSA-N 0.000 description 1
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
- LOVPHSMOAVXQIH-UHFFFAOYSA-N (4-nitrophenyl) hydrogen carbonate Chemical compound OC(=O)OC1=CC=C([N+]([O-])=O)C=C1 LOVPHSMOAVXQIH-UHFFFAOYSA-N 0.000 description 1
- VDSBXXDKCUBMQC-HNGSOEQISA-N (4r,6s)-6-[(e)-2-[2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohexen-1-yl]ethenyl]-4-hydroxyoxan-2-one Chemical compound C1=C(F)C(C)=CC(C=2CC(C)(C)CC(C)(C)C=2\C=C\[C@H]2OC(=O)C[C@H](O)C2)=C1 VDSBXXDKCUBMQC-HNGSOEQISA-N 0.000 description 1
- DMJWENQHWZZWDF-PKOBYXMFSA-N (6aS,13bR)-11-chloro-7-methyl-5,6,6a,8,9,13b-hexahydronaphtho[1,2-a][3]benzazepin-12-ol Chemical compound CN1CCC2=CC(Cl)=C(O)C=C2[C@H]2C3=CC=CC=C3CC[C@H]12 DMJWENQHWZZWDF-PKOBYXMFSA-N 0.000 description 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
- METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
- TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 description 1
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 1
- POPHMOPNVVKGRW-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7-octahydronaphthalene Chemical class C1CCC2CCCCC2=C1 POPHMOPNVVKGRW-UHFFFAOYSA-N 0.000 description 1
- YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- BIXRSCVOWFUPML-UHFFFAOYSA-N 1,3-benzothiazol-2-yl(tributyl)stannane Chemical compound C1=CC=C2SC([Sn](CCCC)(CCCC)CCCC)=NC2=C1 BIXRSCVOWFUPML-UHFFFAOYSA-N 0.000 description 1
- CPHOHOZBKYXBOE-UHFFFAOYSA-N 1,5,6-triphenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C=1C=CC=CC=1C1=NC=2N(C=3C=CC=CC=3)N=CC=2C(=O)N1C1=CC=CC=C1 CPHOHOZBKYXBOE-UHFFFAOYSA-N 0.000 description 1
- YFCXTXUHSLKPHQ-UHFFFAOYSA-N 1-(4-nitrophenyl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound [O-][N+](=O)c1ccc(cc1)-n1ncc2c1nc[nH]c2=O YFCXTXUHSLKPHQ-UHFFFAOYSA-N 0.000 description 1
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 1
- 229940126558 11β-HSD1 inhibitor Drugs 0.000 description 1
- DMDHMKZIUNKSBF-UHFFFAOYSA-N 2,3-dimethylbut-2-enedinitrile Chemical compound N#CC(C)=C(C)C#N DMDHMKZIUNKSBF-UHFFFAOYSA-N 0.000 description 1
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 1
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
- XMQODGUTLZXUGZ-RPBOFIJWSA-N 2-[(3s)-3-[[1-[(2r)-2-ethoxycarbonyl-4-phenylbutyl]cyclopentanecarbonyl]amino]-2-oxo-4,5-dihydro-3h-1-benzazepin-1-yl]acetic acid Chemical group C([C@@H](C(=O)OCC)CC1(CCCC1)C(=O)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XMQODGUTLZXUGZ-RPBOFIJWSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- RCRCTBLIHCHWDZ-DOFZRALJSA-N 2-arachidonoylglycerol Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC(CO)CO RCRCTBLIHCHWDZ-DOFZRALJSA-N 0.000 description 1
- CUJUUWXZAQHCNC-DOFZRALJSA-N 2-arachidonyl glyceryl ether Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCOC(CO)CO CUJUUWXZAQHCNC-DOFZRALJSA-N 0.000 description 1
- GELVZYOEQVJIRR-UHFFFAOYSA-N 2-chloropyrazine Chemical compound ClC1=CN=CC=N1 GELVZYOEQVJIRR-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- JTWHVBNYYWFXSI-UHFFFAOYSA-N 2-nitro-1-phenylethanone Chemical compound [O-][N+](=O)CC(=O)C1=CC=CC=C1 JTWHVBNYYWFXSI-UHFFFAOYSA-N 0.000 description 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 1
- RIZIYJOVNPJCDN-UHFFFAOYSA-N 3-hydroxy-4-phosphonobutanoic acid Chemical class OC(=O)CC(O)CP(O)(O)=O RIZIYJOVNPJCDN-UHFFFAOYSA-N 0.000 description 1
- UIAGMCDKSXEBJQ-IBGZPJMESA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-IBGZPJMESA-N 0.000 description 1
- ZMMOYIXZGHJMNI-UHFFFAOYSA-N 3-oxopropanenitrile Chemical compound O=CCC#N ZMMOYIXZGHJMNI-UHFFFAOYSA-N 0.000 description 1
- CLPFFLWZZBQMAO-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1 CLPFFLWZZBQMAO-UHFFFAOYSA-N 0.000 description 1
- BLBDTBCGPHPIJK-UHFFFAOYSA-N 4-Amino-2-chloropyridine Chemical compound NC1=CC=NC(Cl)=C1 BLBDTBCGPHPIJK-UHFFFAOYSA-N 0.000 description 1
- GWRSATNRNFYMDI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 GWRSATNRNFYMDI-UHFFFAOYSA-N 0.000 description 1
- SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical class COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 description 1
- CBJPATLSUFKXJV-UHFFFAOYSA-N 4-methylbenzenecarboximidoyl chloride Chemical compound CC1=CC=C(C(Cl)=N)C=C1 CBJPATLSUFKXJV-UHFFFAOYSA-N 0.000 description 1
- QDMNYILTVWAKSY-UHFFFAOYSA-N 5-(2-methylphenyl)-6-(4-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C)=CC=C1C(N(C1=O)C=2C(=CC=CC=2)C)=NC2=C1C=NN2C1=CC=CC=C1 QDMNYILTVWAKSY-UHFFFAOYSA-N 0.000 description 1
- CWRJPIDSWJRJIT-UHFFFAOYSA-N 5-(3-chlorophenyl)-6-(2-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC=C1C(N(C1=O)C=2C=C(Cl)C=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 CWRJPIDSWJRJIT-UHFFFAOYSA-N 0.000 description 1
- JPYRSEZMZFVLTC-UHFFFAOYSA-N 5-(3-chlorophenyl)-6-(2-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC=C1C(N(C1=O)C=2C=C(Cl)C=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 JPYRSEZMZFVLTC-UHFFFAOYSA-N 0.000 description 1
- BREBHAMOAQDITI-UHFFFAOYSA-N 5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1C(N(C1=O)C=2C=C(Cl)C=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 BREBHAMOAQDITI-UHFFFAOYSA-N 0.000 description 1
- PFIRLQMLQPBDIH-UHFFFAOYSA-N 5-(3-chlorophenyl)-6-(4-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C)=CC=C1C(N(C1=O)C=2C=C(Cl)C=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 PFIRLQMLQPBDIH-UHFFFAOYSA-N 0.000 description 1
- KCSXPQZNRWZJTJ-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 KCSXPQZNRWZJTJ-UHFFFAOYSA-N 0.000 description 1
- HKKGLBJPWZBGLM-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 HKKGLBJPWZBGLM-UHFFFAOYSA-N 0.000 description 1
- HQBCTHNFYGFTAV-UHFFFAOYSA-N 5-(4-fluorophenyl)-6-(2-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC=C1C(N(C1=O)C=2C=CC(F)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 HQBCTHNFYGFTAV-UHFFFAOYSA-N 0.000 description 1
- FBCKUZYUFVWIBZ-UHFFFAOYSA-N 5-(4-fluorophenyl)-6-(4-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C)=CC=C1C(N(C1=O)C=2C=CC(F)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 FBCKUZYUFVWIBZ-UHFFFAOYSA-N 0.000 description 1
- NKOHRVBBQISBSB-UHFFFAOYSA-N 5-[(4-hydroxyphenyl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1=CC(O)=CC=C1CC1C(=O)NC(=O)S1 NKOHRVBBQISBSB-UHFFFAOYSA-N 0.000 description 1
- WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical compound NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 description 1
- RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- BUKRCICRNQXJCV-UHFFFAOYSA-N 6-(2-fluorophenyl)-5-(2-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=CC=C1F BUKRCICRNQXJCV-UHFFFAOYSA-N 0.000 description 1
- ISKBCNMOTUDCIK-UHFFFAOYSA-N 6-(2-fluorophenyl)-5-(4-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=CC=C1F ISKBCNMOTUDCIK-UHFFFAOYSA-N 0.000 description 1
- VOFVABHNXPTPSK-UHFFFAOYSA-N 6-(2-fluorophenyl)-5-(4-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=CC=C1F VOFVABHNXPTPSK-UHFFFAOYSA-N 0.000 description 1
- ABDXHFUCCHDUCQ-UHFFFAOYSA-N 6-(2-methylphenyl)-5-(4-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=CC=C1C ABDXHFUCCHDUCQ-UHFFFAOYSA-N 0.000 description 1
- ICPPYPLLKATGNJ-UHFFFAOYSA-N 6-(4-bromophenyl)-5-(2,4-dimethylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC(C)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(Br)C=C1 ICPPYPLLKATGNJ-UHFFFAOYSA-N 0.000 description 1
- MXZAXCQRIHTBRX-UHFFFAOYSA-N 6-(4-bromophenyl)-5-(2-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(Br)C=C1 MXZAXCQRIHTBRX-UHFFFAOYSA-N 0.000 description 1
- KHTGFAORQYAINE-UHFFFAOYSA-N 6-(4-bromophenyl)-5-(3-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound ClC1=CC=CC(N2C(C=3C=NN(C=3N=C2C=2C=CC(Br)=CC=2)C=2C=CC=CC=2)=O)=C1 KHTGFAORQYAINE-UHFFFAOYSA-N 0.000 description 1
- WPQHRZBAWPIZPT-UHFFFAOYSA-N 6-(4-bromophenyl)-5-(4-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(Br)C=C1 WPQHRZBAWPIZPT-UHFFFAOYSA-N 0.000 description 1
- MMEHYYYPJXTOED-UHFFFAOYSA-N 6-(4-bromophenyl)-5-(4-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(Br)C=C1 MMEHYYYPJXTOED-UHFFFAOYSA-N 0.000 description 1
- NVLXAGRSNYTNGV-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(2-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(Cl)C=C1 NVLXAGRSNYTNGV-UHFFFAOYSA-N 0.000 description 1
- FCEIPDQFWTUOGR-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(3,5-dimethylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC(C)=CC(N2C(C=3C=NN(C=3N=C2C=2C=CC(Cl)=CC=2)C=2C=CC=CC=2)=O)=C1 FCEIPDQFWTUOGR-UHFFFAOYSA-N 0.000 description 1
- FCYUOLKDUVVDJS-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(4-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(Cl)C=C1 FCYUOLKDUVVDJS-UHFFFAOYSA-N 0.000 description 1
- ODXXXUPCSZTRQJ-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(4-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C)=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(Cl)C=C1 ODXXXUPCSZTRQJ-UHFFFAOYSA-N 0.000 description 1
- VNACOBVZDCLAEV-GXKRWWSZSA-N 6-[2-[[2-[(2s)-2-cyanopyrrolidin-1-yl]-2-oxoethyl]amino]ethylamino]pyridine-3-carbonitrile;dihydrochloride Chemical compound Cl.Cl.N1([C@@H](CCC1)C#N)C(=O)CNCCNC1=CC=C(C#N)C=N1 VNACOBVZDCLAEV-GXKRWWSZSA-N 0.000 description 1
- 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 1
- KAVYKQPEXUKOAG-UHFFFAOYSA-N 8-bromo-1-(4-chlorophenyl)-9-phenyl-2-[4-(trifluoromethyl)phenyl]purin-6-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1N=C(Br)N2C1=CC=CC=C1 KAVYKQPEXUKOAG-UHFFFAOYSA-N 0.000 description 1
- XTAYOIBPZOSPNQ-UHFFFAOYSA-N 8-phenylpurin-2-one Chemical compound N=1C2=NC(=O)N=CC2=NC=1C1=CC=CC=C1 XTAYOIBPZOSPNQ-UHFFFAOYSA-N 0.000 description 1
- 101100230376 Acetivibrio thermocellus (strain ATCC 27405 / DSM 1237 / JCM 9322 / NBRC 103400 / NCIMB 10682 / NRRL B-4536 / VPI 7372) celI gene Proteins 0.000 description 1
- 102000012440 Acetylcholinesterase Human genes 0.000 description 1
- 108010022752 Acetylcholinesterase Proteins 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 1
- 229940123338 Aldosterone synthase inhibitor Drugs 0.000 description 1
- UXOWGYHJODZGMF-QORCZRPOSA-N Aliskiren Chemical compound COCCCOC1=CC(C[C@@H](C[C@H](N)[C@@H](O)C[C@@H](C(C)C)C(=O)NCC(C)(C)C(N)=O)C(C)C)=CC=C1OC UXOWGYHJODZGMF-QORCZRPOSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 229940123413 Angiotensin II antagonist Drugs 0.000 description 1
- 102000005666 Apolipoprotein A-I Human genes 0.000 description 1
- 108010059886 Apolipoprotein A-I Proteins 0.000 description 1
- 101100460776 Arabidopsis thaliana NPY2 gene Proteins 0.000 description 1
- 101100460782 Arabidopsis thaliana NPY4 gene Proteins 0.000 description 1
- 101100460788 Arabidopsis thaliana NPY5 gene Proteins 0.000 description 1
- DTDADHMBRZKXSC-GKASHWOUSA-N Aricine Chemical compound C1=C(OC)C=C2C(CCN3C[C@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 DTDADHMBRZKXSC-GKASHWOUSA-N 0.000 description 1
- 229940122815 Aromatase inhibitor Drugs 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
- XPCFTKFZXHTYIP-PMACEKPBSA-N Benazepril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XPCFTKFZXHTYIP-PMACEKPBSA-N 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- HDKNMBFGYCQPKT-UHFFFAOYSA-N C(=O)OCC.NC=1N=CN(C1)CC1=CC=CC=C1 Chemical compound C(=O)OCC.NC=1N=CN(C1)CC1=CC=CC=C1 HDKNMBFGYCQPKT-UHFFFAOYSA-N 0.000 description 1
- QNGFVRVKKCRECG-UHFFFAOYSA-N C(C)OC(C=NO)=O.[Cl] Chemical compound C(C)OC(C=NO)=O.[Cl] QNGFVRVKKCRECG-UHFFFAOYSA-N 0.000 description 1
- CZSQVSDBRVZRGH-IKUQRVJOSA-N C/C=C\C=C(/C)\N(CC1)CCN1C(N1c(cc2)ccc2Cl)=Nc([n](-c2ccccc2)nc2)c2C1=O Chemical compound C/C=C\C=C(/C)\N(CC1)CCN1C(N1c(cc2)ccc2Cl)=Nc([n](-c2ccccc2)nc2)c2C1=O CZSQVSDBRVZRGH-IKUQRVJOSA-N 0.000 description 1
- 239000002083 C09CA01 - Losartan Substances 0.000 description 1
- 239000002080 C09CA02 - Eprosartan Substances 0.000 description 1
- 239000002947 C09CA04 - Irbesartan Substances 0.000 description 1
- 239000002053 C09CA06 - Candesartan Substances 0.000 description 1
- 239000005537 C09CA07 - Telmisartan Substances 0.000 description 1
- 238000011740 C57BL/6 mouse Methods 0.000 description 1
- 102000009135 CB2 Cannabinoid Receptor Human genes 0.000 description 1
- 108010073376 CB2 Cannabinoid Receptor Proteins 0.000 description 1
- ACGZVOALBQCNGX-UHFFFAOYSA-N CC(C)c(cc1)ccc1C(N(c(cc1)ccc1Cl)C1=O)=Nc2c1[n](CC#N)nc2-c1ccccc1 Chemical compound CC(C)c(cc1)ccc1C(N(c(cc1)ccc1Cl)C1=O)=Nc2c1[n](CC#N)nc2-c1ccccc1 ACGZVOALBQCNGX-UHFFFAOYSA-N 0.000 description 1
- NMXZCHDFUCAQBD-UHFFFAOYSA-N CCOC(c(nc1)c(N)[n]1-c1ccccc1)=O Chemical compound CCOC(c(nc1)c(N)[n]1-c1ccccc1)=O NMXZCHDFUCAQBD-UHFFFAOYSA-N 0.000 description 1
- KILBLDWBGDETCK-UHFFFAOYSA-N CNC(c(c1c2N=C(c(cc3)ccc3Br)N(c(cc3)ccc3Cl)C1=O)n[n]2-c1ccccc1)=O Chemical compound CNC(c(c1c2N=C(c(cc3)ccc3Br)N(c(cc3)ccc3Cl)C1=O)n[n]2-c1ccccc1)=O KILBLDWBGDETCK-UHFFFAOYSA-N 0.000 description 1
- LPQXDXRAAMCLFO-UHFFFAOYSA-N COc1ccc(CNc2nccc(-c(cc3)ccc3C(N3c(cc4)ccc4Cl)=Nc([n](-c4ccccc4)nc4S(C)(=O)=O)c4C3=O)n2)cc1 Chemical compound COc1ccc(CNc2nccc(-c(cc3)ccc3C(N3c(cc4)ccc4Cl)=Nc([n](-c4ccccc4)nc4S(C)(=O)=O)c4C3=O)n2)cc1 LPQXDXRAAMCLFO-UHFFFAOYSA-N 0.000 description 1
- ACMWKHIHAJLRQF-UHFFFAOYSA-N CSCc([n]1-c2ccccc2)nc2c1N=C(c(cc1)ccc1-c1ccccc1)N(c(cc1)ccc1Cl)C2=O Chemical compound CSCc([n]1-c2ccccc2)nc2c1N=C(c(cc1)ccc1-c1ccccc1)N(c(cc1)ccc1Cl)C2=O ACMWKHIHAJLRQF-UHFFFAOYSA-N 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- ZCKAMNXUHHNZLN-UHFFFAOYSA-N Chlorphentermine Chemical compound CC(C)(N)CC1=CC=C(Cl)C=C1 ZCKAMNXUHHNZLN-UHFFFAOYSA-N 0.000 description 1
- 229920001268 Cholestyramine Polymers 0.000 description 1
- ZUZBCIXCPNLAOU-UHFFFAOYSA-N Cl[NH] Chemical compound Cl[NH] ZUZBCIXCPNLAOU-UHFFFAOYSA-N 0.000 description 1
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 108010022152 Corticotropin-Releasing Hormone Proteins 0.000 description 1
- 102000034534 Cotransporters Human genes 0.000 description 1
- 108020003264 Cotransporters Proteins 0.000 description 1
- 241000699802 Cricetulus griseus Species 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-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
- 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 description 1
- 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 description 1
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 108010067722 Dipeptidyl Peptidase 4 Proteins 0.000 description 1
- JRWZLRBJNMZMFE-UHFFFAOYSA-N Dobutamine Chemical compound C=1C=C(O)C(O)=CC=1CCNC(C)CCC1=CC=C(O)C=C1 JRWZLRBJNMZMFE-UHFFFAOYSA-N 0.000 description 1
- 108010061435 Enalapril Proteins 0.000 description 1
- 102100029112 Endothelin-converting enzyme 1 Human genes 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 description 1
- 108010011459 Exenatide Proteins 0.000 description 1
- WRWCAQNPEXYGJK-PKNBQFBNSA-N GW 0791 Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C1CCCC2=C1C=C(\C=C\C(O)=O)O2 WRWCAQNPEXYGJK-PKNBQFBNSA-N 0.000 description 1
- 102000011392 Galanin receptor Human genes 0.000 description 1
- 108050001605 Galanin receptor Proteins 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 108010016122 Ghrelin Receptors Proteins 0.000 description 1
- FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 108010046163 Glycogen Phosphorylase Proteins 0.000 description 1
- 102000007390 Glycogen Phosphorylase Human genes 0.000 description 1
- 102100039256 Growth hormone secretagogue receptor type 1 Human genes 0.000 description 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
- 239000004866 Hashish Substances 0.000 description 1
- 101000685982 Homo sapiens NAD(+) hydrolase SARM1 Proteins 0.000 description 1
- 101000684208 Homo sapiens Prolyl endopeptidase FAP Proteins 0.000 description 1
- 102000004286 Hydroxymethylglutaryl CoA Reductases Human genes 0.000 description 1
- 108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 1
- 206010020710 Hyperphagia Diseases 0.000 description 1
- 206010021113 Hypothermia Diseases 0.000 description 1
- 229940122355 Insulin sensitizer Drugs 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000005517 L01XE01 - Imatinib Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000007177 Left Ventricular Hypertrophy Diseases 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229940086609 Lipase inhibitor Drugs 0.000 description 1
- 108010007859 Lisinopril Proteins 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 108091022875 Microtubule Proteins 0.000 description 1
- 102000029749 Microtubule Human genes 0.000 description 1
- 102000003979 Mineralocorticoid Receptors Human genes 0.000 description 1
- 108090000375 Mineralocorticoid Receptors Proteins 0.000 description 1
- UWWDHYUMIORJTA-HSQYWUDLSA-N Moexipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC(OC)=C(OC)C=C2C1)C(O)=O)CC1=CC=CC=C1 UWWDHYUMIORJTA-HSQYWUDLSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- GIYXAJPCNFJEHY-UHFFFAOYSA-N N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]-1-propanamine hydrochloride (1:1) Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=C(C(F)(F)F)C=C1 GIYXAJPCNFJEHY-UHFFFAOYSA-N 0.000 description 1
- 125000000815 N-oxide group Chemical group 0.000 description 1
- 102100023356 NAD(+) hydrolase SARM1 Human genes 0.000 description 1
- 101150027439 NPY1 gene Proteins 0.000 description 1
- 101150111774 NPY5R gene Proteins 0.000 description 1
- WJBLNOPPDWQMCH-MBPVOVBZSA-N Nalmefene Chemical compound N1([C@@H]2CC3=CC=C(C=4O[C@@H]5[C@](C3=4)([C@]2(CCC5=C)O)CC1)O)CC1CC1 WJBLNOPPDWQMCH-MBPVOVBZSA-N 0.000 description 1
- NJVCXQCITAPQJC-UHFFFAOYSA-N Nc([n](-c1ccccc1)nc1)c1C(Nc(cc1)ccc1Cl)=O Chemical compound Nc([n](-c1ccccc1)nc1)c1C(Nc(cc1)ccc1Cl)=O NJVCXQCITAPQJC-UHFFFAOYSA-N 0.000 description 1
- BFMGSMOYBHOHGI-UHFFFAOYSA-N Nc([n](-c1ccccc1)nc1)c1C(O)=O Chemical compound Nc([n](-c1ccccc1)nc1)c1C(O)=O BFMGSMOYBHOHGI-UHFFFAOYSA-N 0.000 description 1
- ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 description 1
- CFFASQUFNILQDD-UHFFFAOYSA-N O=C(c1c(N2)[n](-c3ccccc3)nc1)N(c(cc1)ccc1Cl)C2=O Chemical compound O=C(c1c(N2)[n](-c3ccccc3)nc1)N(c(cc1)ccc1Cl)C2=O CFFASQUFNILQDD-UHFFFAOYSA-N 0.000 description 1
- MYKZLFFVCRRJSJ-UHFFFAOYSA-N O=C(c1c(NC(c(c(Cl)c2)ccc2Cl)=O)[n](Cc2ccccc2)cn1)Nc(cc1)ccc1Cl Chemical compound O=C(c1c(NC(c(c(Cl)c2)ccc2Cl)=O)[n](Cc2ccccc2)cn1)Nc(cc1)ccc1Cl MYKZLFFVCRRJSJ-UHFFFAOYSA-N 0.000 description 1
- XLGMFZWHFVYQGO-UHFFFAOYSA-N O=C(c1cc(-[n]2c(N=C(c(cc3)ccc3-c3ccccc3)N(c(cc3)ccc3Cl)C3=O)c3nc2)ccc1)Nc1n[o]cc1 Chemical compound O=C(c1cc(-[n]2c(N=C(c(cc3)ccc3-c3ccccc3)N(c(cc3)ccc3Cl)C3=O)c3nc2)ccc1)Nc1n[o]cc1 XLGMFZWHFVYQGO-UHFFFAOYSA-N 0.000 description 1
- VKLHTMKAPREVND-UHFFFAOYSA-N O=C1N(c(cc2)ccc2Cl)C(N(CC2)CC[N-]2c2ccccc2)=Nc2c1cn[n]2-c1ccccc1 Chemical compound O=C1N(c(cc2)ccc2Cl)C(N(CC2)CC[N-]2c2ccccc2)=Nc2c1cn[n]2-c1ccccc1 VKLHTMKAPREVND-UHFFFAOYSA-N 0.000 description 1
- GREXLJIURDIPJP-UHFFFAOYSA-N O=C1N(c(cc2)ccc2Cl)C(c(c(Cl)c2)ccc2Cl)=Nc2c1nc[n]2Cc1ccccc1 Chemical compound O=C1N(c(cc2)ccc2Cl)C(c(c(Cl)c2)ccc2Cl)=Nc2c1nc[n]2Cc1ccccc1 GREXLJIURDIPJP-UHFFFAOYSA-N 0.000 description 1
- HCPZKZUKGNZREZ-UHFFFAOYSA-N O=C1N(c(cc2)ccc2Cl)C(c(cc2)ccc2-c2ccccc2)=Nc2c1nc(CBr)[n]2-c1ccccc1 Chemical compound O=C1N(c(cc2)ccc2Cl)C(c(cc2)ccc2-c2ccccc2)=Nc2c1nc(CBr)[n]2-c1ccccc1 HCPZKZUKGNZREZ-UHFFFAOYSA-N 0.000 description 1
- 108010055723 PDGF receptor tyrosine kinase Proteins 0.000 description 1
- 108010015181 PPAR delta Proteins 0.000 description 1
- 108010016731 PPAR gamma Proteins 0.000 description 1
- 102000000536 PPAR gamma Human genes 0.000 description 1
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 1
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 1
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 1
- 229940080774 Peroxisome proliferator-activated receptor gamma agonist Drugs 0.000 description 1
- MFOCDFTXLCYLKU-CMPLNLGQSA-N Phendimetrazine Chemical compound O1CCN(C)[C@@H](C)[C@@H]1C1=CC=CC=C1 MFOCDFTXLCYLKU-CMPLNLGQSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
- 102000035554 Proglucagon Human genes 0.000 description 1
- 108010058003 Proglucagon Proteins 0.000 description 1
- 102000001253 Protein Kinase Human genes 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229940123934 Reductase inhibitor Drugs 0.000 description 1
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
- AJLFOPYRIVGYMJ-UHFFFAOYSA-N SJ000287055 Natural products C12C(OC(=O)C(C)CC)CCC=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 AJLFOPYRIVGYMJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000006619 Stille reaction Methods 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 102000018692 Sulfonylurea Receptors Human genes 0.000 description 1
- 108010091821 Sulfonylurea Receptors Proteins 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 108010036928 Thiorphan Proteins 0.000 description 1
- 229940122388 Thrombin inhibitor Drugs 0.000 description 1
- 239000000365 Topoisomerase I Inhibitor Substances 0.000 description 1
- 239000000317 Topoisomerase II Inhibitor Substances 0.000 description 1
- NGBFQHCMQULJNZ-UHFFFAOYSA-N Torsemide Chemical compound CC(C)NC(=O)NS(=O)(=O)C1=CN=CC=C1NC1=CC=CC(C)=C1 NGBFQHCMQULJNZ-UHFFFAOYSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- BXNCIERBDJYIQT-PRDVQWLOSA-N [(2r,3s,4s,5r,6s)-6-[2-[3-(1-benzofuran-5-yl)propanoyl]-3-hydroxy-5-methylphenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl methyl carbonate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)OC)O[C@H]1OC1=CC(C)=CC(O)=C1C(=O)CCC1=CC=C(OC=C2)C2=C1 BXNCIERBDJYIQT-PRDVQWLOSA-N 0.000 description 1
- AEDMQUAPBVOJNN-UHFFFAOYSA-N [3-[2-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,3-thiazol-5-yl]-1,2,4-oxadiazol-5-yl]methanol Chemical compound O1C(CO)=NC(C=2SC(=NC=2)N2CCC(CC2)OC=2C(=CC=CC=2)C(F)(F)F)=N1 AEDMQUAPBVOJNN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- AFCGFAGUEYAMAO-UHFFFAOYSA-N acamprosate Chemical compound CC(=O)NCCCS(O)(=O)=O AFCGFAGUEYAMAO-UHFFFAOYSA-N 0.000 description 1
- 229960004047 acamprosate Drugs 0.000 description 1
- 229960002632 acarbose Drugs 0.000 description 1
- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 1
- 229960002122 acebutolol Drugs 0.000 description 1
- GOEMGAFJFRBGGG-UHFFFAOYSA-N acebutolol Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 GOEMGAFJFRBGGG-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 229940022698 acetylcholinesterase Drugs 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 102000005421 acetyltransferase Human genes 0.000 description 1
- 108020002494 acetyltransferase Proteins 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 108060000200 adenylate cyclase Proteins 0.000 description 1
- 102000030621 adenylate cyclase Human genes 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 208000029650 alcohol withdrawal Diseases 0.000 description 1
- 229960002478 aldosterone Drugs 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229960004601 aliskiren Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical compound [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 0.000 description 1
- 238000010640 amide synthesis reaction Methods 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 1
- HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 description 1
- 229960000528 amlodipine Drugs 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 description 1
- 229960002932 anastrozole Drugs 0.000 description 1
- 239000002333 angiotensin II receptor antagonist Substances 0.000 description 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
- 229940046836 anti-estrogen Drugs 0.000 description 1
- 230000001833 anti-estrogenic effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000003502 anti-nociceptive effect Effects 0.000 description 1
- 239000000883 anti-obesity agent Substances 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 239000003524 antilipemic agent Substances 0.000 description 1
- 239000002814 antineoplastic antimetabolite Substances 0.000 description 1
- 229940125710 antiobesity agent Drugs 0.000 description 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 229960004046 apomorphine Drugs 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- UHDJCSZGZJGMDR-UHFFFAOYSA-N aricine Natural products COC(=O)C1=COC(C)C2(C)CN3CCc4c([nH]c5ccc(OC)cc45)C3(C)CC12C UHDJCSZGZJGMDR-UHFFFAOYSA-N 0.000 description 1
- 239000003886 aromatase inhibitor Substances 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 150000004646 arylidenes Chemical group 0.000 description 1
- 229960002274 atenolol Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960005370 atorvastatin Drugs 0.000 description 1
- AQRHTGSVDQECPZ-UHFFFAOYSA-N azane;lithium Chemical compound [Li].N AQRHTGSVDQECPZ-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229960004530 benazepril Drugs 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 229960002837 benzphetamine Drugs 0.000 description 1
- YXKTVDFXDRQTKV-HNNXBMFYSA-N benzphetamine Chemical compound C([C@H](C)N(C)CC=1C=CC=CC=1)C1=CC=CC=C1 YXKTVDFXDRQTKV-HNNXBMFYSA-N 0.000 description 1
- KKBIUAUSZKGNOA-HNAYVOBHSA-N benzyl (2s)-2-[[(2s)-2-(acetylsulfanylmethyl)-3-(1,3-benzodioxol-5-yl)propanoyl]amino]propanoate Chemical compound O=C([C@@H](NC(=O)[C@@H](CSC(C)=O)CC=1C=C2OCOC2=CC=1)C)OCC1=CC=CC=C1 KKBIUAUSZKGNOA-HNAYVOBHSA-N 0.000 description 1
- UIEATEWHFDRYRU-UHFFFAOYSA-N bepridil Chemical compound C1CCCN1C(COCC(C)C)CN(C=1C=CC=CC=1)CC1=CC=CC=C1 UIEATEWHFDRYRU-UHFFFAOYSA-N 0.000 description 1
- 229960003665 bepridil Drugs 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229960004324 betaxolol Drugs 0.000 description 1
- CHDPSNLJFOQTRK-UHFFFAOYSA-N betaxolol hydrochloride Chemical compound [Cl-].C1=CC(OCC(O)C[NH2+]C(C)C)=CC=C1CCOCC1CC1 CHDPSNLJFOQTRK-UHFFFAOYSA-N 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 229960002781 bisoprolol Drugs 0.000 description 1
- VHYCDWMUTMEGQY-UHFFFAOYSA-N bisoprolol Chemical compound CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1 VHYCDWMUTMEGQY-UHFFFAOYSA-N 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 1
- 229960002802 bromocriptine Drugs 0.000 description 1
- MFIUDWFSVDFDDY-UHFFFAOYSA-M butyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC)C1=CC=CC=C1 MFIUDWFSVDFDDY-UHFFFAOYSA-M 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229960000932 candesartan Drugs 0.000 description 1
- SGZAIDDFHDDFJU-UHFFFAOYSA-N candesartan Chemical compound CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SGZAIDDFHDDFJU-UHFFFAOYSA-N 0.000 description 1
- 229930003827 cannabinoid Natural products 0.000 description 1
- 239000003557 cannabinoid Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229960000830 captopril Drugs 0.000 description 1
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229960005110 cerivastatin Drugs 0.000 description 1
- SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 description 1
- GPUADMRJQVPIAS-QCVDVZFFSA-M cerivastatin sodium Chemical compound [Na+].COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 GPUADMRJQVPIAS-QCVDVZFFSA-M 0.000 description 1
- MVCQKIKWYUURMU-UHFFFAOYSA-N cetilistat Chemical compound C1=C(C)C=C2C(=O)OC(OCCCCCCCCCCCCCCCC)=NC2=C1 MVCQKIKWYUURMU-UHFFFAOYSA-N 0.000 description 1
- 229950002397 cetilistat Drugs 0.000 description 1
- JUFFVKRROAPVBI-PVOYSMBESA-N chembl1210015 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)N[C@H]1[C@@H]([C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO[C@]3(O[C@@H](C[C@H](O)[C@H](O)CO)[C@H](NC(C)=O)[C@@H](O)C3)C(O)=O)O2)O)[C@@H](CO)O1)NC(C)=O)C(=O)NCC(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 JUFFVKRROAPVBI-PVOYSMBESA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229960002155 chlorothiazide Drugs 0.000 description 1
- 229950007046 chlorphentermine Drugs 0.000 description 1
- 230000001906 cholesterol absorption Effects 0.000 description 1
- NCNFDKWULDWJDS-OAHLLOKOSA-N cilansetron Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C=3N4CCCC=3C=CC=2)=C4CC1 NCNFDKWULDWJDS-OAHLLOKOSA-N 0.000 description 1
- 229960002099 cilansetron Drugs 0.000 description 1
- DCSUBABJRXZOMT-IRLDBZIGSA-N cisapride Chemical compound C([C@@H]([C@@H](CC1)NC(=O)C=2C(=CC(N)=C(Cl)C=2)OC)OC)N1CCCOC1=CC=C(F)C=C1 DCSUBABJRXZOMT-IRLDBZIGSA-N 0.000 description 1
- 229960005132 cisapride Drugs 0.000 description 1
- DCSUBABJRXZOMT-UHFFFAOYSA-N cisapride Natural products C1CC(NC(=O)C=2C(=CC(N)=C(Cl)C=2)OC)C(OC)CN1CCCOC1=CC=C(F)C=C1 DCSUBABJRXZOMT-UHFFFAOYSA-N 0.000 description 1
- TZWKUQDQKPYNLL-UHFFFAOYSA-N cloforex Chemical compound CCOC(=O)NC(C)(C)CC1=CC=C(Cl)C=C1 TZWKUQDQKPYNLL-UHFFFAOYSA-N 0.000 description 1
- 229950008294 cloforex Drugs 0.000 description 1
- 229960002896 clonidine Drugs 0.000 description 1
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000001149 cognitive effect Effects 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229940124301 concurrent medication Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- OPHUWKNKFYBPDR-UHFFFAOYSA-N copper lithium Chemical compound [Li].[Cu] OPHUWKNKFYBPDR-UHFFFAOYSA-N 0.000 description 1
- 229940111134 coxibs Drugs 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- 239000003255 cyclooxygenase 2 inhibitor Substances 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
- 229950003040 dalvastatin Drugs 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical class CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 1
- 150000002013 dioxins Chemical class 0.000 description 1
- ONDPGJBEBGWAKI-UHFFFAOYSA-N diphenylphosphane;propane Chemical compound CCC.C=1C=CC=CC=1PC1=CC=CC=C1 ONDPGJBEBGWAKI-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 108010083220 ditekiren Proteins 0.000 description 1
- 229950010513 ditekiren Drugs 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 229960001089 dobutamine Drugs 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 229950009714 ecopipam Drugs 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960000873 enalapril Drugs 0.000 description 1
- GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- JUKPWJGBANNWMW-VWBFHTRKSA-N eplerenone Chemical compound C([C@@H]1[C@]2(C)C[C@H]3O[C@]33[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)C(=O)OC)C[C@@]21CCC(=O)O1 JUKPWJGBANNWMW-VWBFHTRKSA-N 0.000 description 1
- 229960001208 eplerenone Drugs 0.000 description 1
- OROAFUQRIXKEMV-LDADJPATSA-N eprosartan Chemical compound C=1C=C(C(O)=O)C=CC=1CN1C(CCCC)=NC=C1\C=C(C(O)=O)/CC1=CC=CS1 OROAFUQRIXKEMV-LDADJPATSA-N 0.000 description 1
- 229960004563 eprosartan Drugs 0.000 description 1
- 239000000328 estrogen antagonist Substances 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
- AVOLMBLBETYQHX-UHFFFAOYSA-N etacrynic acid Chemical compound CCC(=C)C(=O)C1=CC=C(OCC(O)=O)C(Cl)=C1Cl AVOLMBLBETYQHX-UHFFFAOYSA-N 0.000 description 1
- 229960003199 etacrynic acid Drugs 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- YVPJCJLMRRTDMQ-UHFFFAOYSA-N ethyl diazoacetate Chemical compound CCOC(=O)C=[N+]=[N-] YVPJCJLMRRTDMQ-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 229960001519 exenatide Drugs 0.000 description 1
- 229950011548 fadrozole Drugs 0.000 description 1
- 229940043259 farnesol Drugs 0.000 description 1
- 229930002886 farnesol Natural products 0.000 description 1
- 229950005203 fasidotril Drugs 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229960003580 felodipine Drugs 0.000 description 1
- HEXAHJRXDZDVLR-HZPDHXFCSA-N fenisorex Chemical compound C1([C@@H]2C3=CC(F)=CC=C3C[C@@H](O2)NC)=CC=CC=C1 HEXAHJRXDZDVLR-HZPDHXFCSA-N 0.000 description 1
- 229950000734 fenisorex Drugs 0.000 description 1
- 229960000389 fluoxetine hydrochloride Drugs 0.000 description 1
- 229960003765 fluvastatin Drugs 0.000 description 1
- CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 description 1
- 229960004038 fluvoxamine Drugs 0.000 description 1
- 229960002490 fosinopril Drugs 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229960003883 furosemide Drugs 0.000 description 1
- 229960002870 gabapentin Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229960004580 glibenclamide Drugs 0.000 description 1
- ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 1
- 229960001381 glipizide Drugs 0.000 description 1
- 239000003877 glucagon like peptide 1 receptor agonist Substances 0.000 description 1
- 150000002310 glutaric acid derivatives Chemical class 0.000 description 1
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- FVMMOSQBOWPRQW-UHFFFAOYSA-N heterophylline Natural products CC(=O)OC1C2(C)C(OC(=O)C=3C=CC=CC=3)CC(C(O3)(C)C)C(OC(=O)C=4C=NC=CC=4)C32C(C)CC1OC(=O)C1=CC=CN=C1 FVMMOSQBOWPRQW-UHFFFAOYSA-N 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 1
- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 description 1
- 229960002411 imatinib Drugs 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000004041 inotropic agent Substances 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 229940125425 inverse agonist Drugs 0.000 description 1
- 229960002198 irbesartan Drugs 0.000 description 1
- YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 102000005861 leptin receptors Human genes 0.000 description 1
- 108010019813 leptin receptors Proteins 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229960002394 lisinopril Drugs 0.000 description 1
- RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 239000002171 loop diuretic Substances 0.000 description 1
- 229960004773 losartan Drugs 0.000 description 1
- KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 1
- 231100000863 loss of memory Toxicity 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 210000003563 lymphoid tissue Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229950004994 meglitinide Drugs 0.000 description 1
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 description 1
- 229960004640 memantine Drugs 0.000 description 1
- 210000000713 mesentery Anatomy 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 229960002237 metoprolol Drugs 0.000 description 1
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 1
- AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 description 1
- 229950009116 mevastatin Drugs 0.000 description 1
- BOZILQFLQYBIIY-UHFFFAOYSA-N mevastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CCC=C21 BOZILQFLQYBIIY-UHFFFAOYSA-N 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- PZRHRDRVRGEVNW-UHFFFAOYSA-N milrinone Chemical compound N1C(=O)C(C#N)=CC(C=2C=CN=CC=2)=C1C PZRHRDRVRGEVNW-UHFFFAOYSA-N 0.000 description 1
- 229960003574 milrinone Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229960005170 moexipril Drugs 0.000 description 1
- 230000000407 monoamine reuptake Effects 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- CMPKKWSDWROOKE-UHFFFAOYSA-N n-(4-bromophenyl)-4-methylbenzenecarboximidoyl chloride Chemical compound C1=CC(C)=CC=C1C(Cl)=NC1=CC=C(Br)C=C1 CMPKKWSDWROOKE-UHFFFAOYSA-N 0.000 description 1
- VVVJJGMCVOLVFK-UHFFFAOYSA-N n-(4-chlorophenyl)-4-(2-chloropyrimidin-4-yl)benzamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CC=C(C=2N=C(Cl)N=CC=2)C=C1 VVVJJGMCVOLVFK-UHFFFAOYSA-N 0.000 description 1
- VWPOSFSPZNDTMJ-UCWKZMIHSA-N nadolol Chemical compound C1[C@@H](O)[C@@H](O)CC2=C1C=CC=C2OCC(O)CNC(C)(C)C VWPOSFSPZNDTMJ-UCWKZMIHSA-N 0.000 description 1
- 229960004255 nadolol Drugs 0.000 description 1
- 229960005297 nalmefene Drugs 0.000 description 1
- OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 description 1
- 229960000698 nateglinide Drugs 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 229960001783 nicardipine Drugs 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 238000002670 nicotine replacement therapy Methods 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 229960000715 nimodipine Drugs 0.000 description 1
- 229960000227 nisoldipine Drugs 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 1
- 229960005017 olanzapine Drugs 0.000 description 1
- LVRLSYPNFFBYCZ-VGWMRTNUSA-N omapatrilat Chemical compound C([C@H](S)C(=O)N[C@H]1CCS[C@H]2CCC[C@H](N2C1=O)C(=O)O)C1=CC=CC=C1 LVRLSYPNFFBYCZ-VGWMRTNUSA-N 0.000 description 1
- 229950000973 omapatrilat Drugs 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 239000003401 opiate antagonist Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 235000020830 overeating Nutrition 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229960002296 paroxetine Drugs 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 229960002582 perindopril Drugs 0.000 description 1
- IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 230000008855 peristalsis Effects 0.000 description 1
- 229960000436 phendimetrazine Drugs 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical class ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- PZJBWSQQDMRZHY-UHFFFAOYSA-N picilorex Chemical compound CC1NC(C2CC2)CC1C1=CC=C(Cl)C=C1 PZJBWSQQDMRZHY-UHFFFAOYSA-N 0.000 description 1
- 229950003624 picilorex Drugs 0.000 description 1
- 229960005095 pioglitazone Drugs 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 229960002797 pitavastatin Drugs 0.000 description 1
- VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 210000003240 portal vein Anatomy 0.000 description 1
- 230000007943 positive regulation of appetite Effects 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 229960002965 pravastatin Drugs 0.000 description 1
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 description 1
- 229960001233 pregabalin Drugs 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 238000002331 protein detection Methods 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 1
- 229960003908 pseudoephedrine Drugs 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 229940073095 questran Drugs 0.000 description 1
- 229960001455 quinapril Drugs 0.000 description 1
- JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 229960003401 ramipril Drugs 0.000 description 1
- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 1
- ZLQMRLSBXKQKMG-UHFFFAOYSA-N rauniticine Natural products COC(=O)C1=CC2CC3N(CCc4c3[nH]c5ccccc45)CC2C(C)O1 ZLQMRLSBXKQKMG-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 229940124617 receptor tyrosine kinase inhibitor Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000002461 renin inhibitor Substances 0.000 description 1
- 229940086526 renin-inhibitors Drugs 0.000 description 1
- 229960002354 repaglinide Drugs 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 1
- 229960001534 risperidone Drugs 0.000 description 1
- 229960004586 rosiglitazone Drugs 0.000 description 1
- 229950001780 sampatrilat Drugs 0.000 description 1
- 108010033693 saxagliptin Proteins 0.000 description 1
- QGJUIPDUBHWZPV-SGTAVMJGSA-N saxagliptin Chemical compound C1C(C2)CC(C3)CC2(O)CC13[C@H](N)C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21 QGJUIPDUBHWZPV-SGTAVMJGSA-N 0.000 description 1
- 229960004937 saxagliptin Drugs 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000000580 secretagogue effect Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000849 selective androgen receptor modulator Substances 0.000 description 1
- 239000000333 selective estrogen receptor modulator Substances 0.000 description 1
- 229940095743 selective estrogen receptor modulator Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000952 serotonin receptor agonist Substances 0.000 description 1
- 229960002073 sertraline Drugs 0.000 description 1
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229960002855 simvastatin Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229960002370 sotalol Drugs 0.000 description 1
- ZBMZVLHSJCTVON-UHFFFAOYSA-N sotalol Chemical compound CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 ZBMZVLHSJCTVON-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000004059 squalene synthase inhibitor Substances 0.000 description 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 229950009390 symclosene Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- IKBKZGMPCYNSLU-RGVLZGJSSA-N tegaserod Chemical compound C1=C(OC)C=C2C(/C=N/NC(=N)NCCCCC)=CNC2=C1 IKBKZGMPCYNSLU-RGVLZGJSSA-N 0.000 description 1
- 229960002876 tegaserod Drugs 0.000 description 1
- 229960005187 telmisartan Drugs 0.000 description 1
- UZQBKCWYZBHBOW-YIPNQBBMSA-N terlakiren Chemical compound C([C@@H](C(=O)N[C@@H](CSC)C(=O)N[C@@H](CC1CCCCC1)[C@@H](O)C(=O)OC(C)C)NC(=O)N1CCOCC1)C1=CC=CC=C1 UZQBKCWYZBHBOW-YIPNQBBMSA-N 0.000 description 1
- 108010069247 terlakiren Proteins 0.000 description 1
- 229950003204 terlakiren Drugs 0.000 description 1
- SASWSEQJAITMKS-JJNNLWIXSA-N tert-butyl (2s)-2-[[(2s)-1-[[(2s)-1-[[(4s,5s,7s)-5-hydroxy-2,8-dimethyl-7-[[(2s,3s)-3-methyl-1-oxo-1-(pyridin-2-ylmethylamino)pentan-2-yl]carbamoyl]nonan-4-yl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]-methylamino]-1-oxo-3-phenylpropan-2-yl]carbamoyl]p Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)[C@@H](O)C[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC=1N=CC=CC=1)C(C)C)N(C)C(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H]1N(CCC1)C(=O)OC(C)(C)C)C1=CN=CN1 SASWSEQJAITMKS-JJNNLWIXSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- LJJKNPQAGWVLDQ-SNVBAGLBSA-N thiorphan Chemical group OC(=O)CNC(=O)[C@@H](CS)CC1=CC=CC=C1 LJJKNPQAGWVLDQ-SNVBAGLBSA-N 0.000 description 1
- 239000003868 thrombin inhibitor Substances 0.000 description 1
- 230000001519 thymoleptic effect Effects 0.000 description 1
- 108090000721 thyroid hormone receptors Proteins 0.000 description 1
- 102000004217 thyroid hormone receptors Human genes 0.000 description 1
- 229960004605 timolol Drugs 0.000 description 1
- 229960005461 torasemide Drugs 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
- UNEPXPMBVGDXGH-UHFFFAOYSA-N tributyl(pyridin-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=NC=C1 UNEPXPMBVGDXGH-UHFFFAOYSA-N 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- ZXIBCJHYVWYIKI-PZJWPPBQSA-N ximelagatran Chemical compound C1([C@@H](NCC(=O)OCC)C(=O)N2[C@@H](CC2)C(=O)NCC=2C=CC(=CC=2)C(\N)=N\O)CCCCC1 ZXIBCJHYVWYIKI-PZJWPPBQSA-N 0.000 description 1
- 229960001522 ximelagatran Drugs 0.000 description 1
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 1
- 229960000607 ziprasidone Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/04—Drugs for disorders of the urinary system for urolithiasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/22—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/28—Oxygen atom
- C07D473/30—Oxygen atom attached in position 6, e.g. hypoxanthine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Dermatology (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Gastroenterology & Hepatology (AREA)
- Child & Adolescent Psychology (AREA)
- Vascular Medicine (AREA)
- Addiction (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62250804P | 2004-10-26 | 2004-10-26 | |
| US60/622,508 | 2004-10-26 | ||
| US67267005P | 2005-04-18 | 2005-04-18 | |
| US60/672,670 | 2005-04-18 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2005800368900A Division CN101048408B (zh) | 2004-10-26 | 2005-10-26 | 作为大麻素受体1活性抑制剂的化合物和组合物 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102241680A true CN102241680A (zh) | 2011-11-16 |
Family
ID=36228382
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011101210450A Pending CN102241680A (zh) | 2004-10-26 | 2005-10-26 | 作为大麻素受体1活性抑制剂的化合物和组合物 |
| CN2005800368900A Expired - Fee Related CN101048408B (zh) | 2004-10-26 | 2005-10-26 | 作为大麻素受体1活性抑制剂的化合物和组合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2005800368900A Expired - Fee Related CN101048408B (zh) | 2004-10-26 | 2005-10-26 | 作为大麻素受体1活性抑制剂的化合物和组合物 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US8158634B2 (enExample) |
| EP (1) | EP1807429A4 (enExample) |
| JP (2) | JP2008518016A (enExample) |
| KR (1) | KR100919524B1 (enExample) |
| CN (2) | CN102241680A (enExample) |
| AR (1) | AR051596A1 (enExample) |
| AU (2) | AU2005299421B2 (enExample) |
| BR (1) | BRPI0517015A (enExample) |
| CA (2) | CA2581225C (enExample) |
| EC (1) | ECSP077421A (enExample) |
| IL (1) | IL182527A0 (enExample) |
| IN (1) | IN2007DN02514A (enExample) |
| MA (1) | MA28937B1 (enExample) |
| MX (1) | MX2007004936A (enExample) |
| NO (1) | NO20072352L (enExample) |
| PE (1) | PE20060599A1 (enExample) |
| RU (1) | RU2431635C2 (enExample) |
| TN (1) | TNSN07161A1 (enExample) |
| TW (1) | TW200630096A (enExample) |
| WO (1) | WO2006047516A2 (enExample) |
Families Citing this family (76)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1599468E (pt) | 2003-01-14 | 2008-01-14 | Arena Pharm Inc | Derivados de arilo e heteroarilo 1,2,3.-trissubstituídos comomoduladores do metabolismo, e profilaxia e tratamento dedesordens relacionadas tais como diabetes e hiperglicemia |
| EP2287165A3 (en) | 2003-07-14 | 2011-06-22 | Arena Pharmaceuticals, Inc. | Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto |
| JP2007519754A (ja) * | 2004-01-30 | 2007-07-19 | スミスクライン ビーチャム コーポレーション | 化合物 |
| AR051596A1 (es) * | 2004-10-26 | 2007-01-24 | Irm Llc | Compuestos heterociclicos condensados nitrogenados como inhibidores de la actividad del receptor canabinoide 1; composiciones farmaceuticas que los contienen y su empleo en la preparacion de medicamentos para el tratamiento de trastornos alimentarios |
| GB0506147D0 (en) * | 2005-03-24 | 2005-05-04 | Merck Sharp & Dohme | Therapeutic agents |
| JP2009536608A (ja) * | 2005-05-11 | 2009-10-15 | メルク シャープ エンド ドーム リミテッド | バニロイド−1受容体(vr1)の機能を調節する2,3−置換縮合二環式ピリミジン4−(3h)−オン |
| WO2007000655A2 (en) * | 2005-06-28 | 2007-01-04 | Orchid Research Laboratories Limited | Novel pyrazolopyrimidinone derivatives |
| EP1954283A2 (en) | 2005-11-04 | 2008-08-13 | Hydra Biosciences, Inc. | Compounds for modulating trpv3 function |
| WO2007063946A1 (ja) * | 2005-11-30 | 2007-06-07 | Fujifilm Ri Pharma Co., Ltd. | アミロイドの凝集及び/又は沈着に起因する疾患の診断薬及び治療薬 |
| JP5253374B2 (ja) * | 2006-03-30 | 2013-07-31 | アイアールエム・リミテッド・ライアビリティ・カンパニー | カンナビノイド受容体1活性の阻害剤としてのアゾロピリミジン類 |
| BRPI0715160A2 (pt) | 2006-08-08 | 2013-06-11 | Sanofi Aventis | imidazolidina-2,4-dionas substituÍdas por arilamimoaril-alquil-, processo para preparÁ-las, medicamentos compeendendo estes compostos, e seu uso |
| MX2009002066A (es) * | 2006-08-23 | 2009-03-06 | Neurogen Corp | Analogos de 2-fenoxipirimidinona. |
| WO2008134300A1 (en) * | 2007-04-26 | 2008-11-06 | Irm Llc | Compounds and compositions as inhibitors of cannabinoid receptor 1 activity |
| WO2008140750A1 (en) * | 2007-05-10 | 2008-11-20 | Hydra Biosciences Inc. | Compounds for modulating trpv3 function |
| EP2170350B1 (en) * | 2007-06-21 | 2013-09-11 | Cara Therapeutics, Inc. | Substituted imidazoheterocycles |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| CN101801954B (zh) | 2007-09-20 | 2013-10-09 | Irm责任有限公司 | 作为gpr119活性调节剂的化合物和组合物 |
| US20120015957A1 (en) * | 2007-12-17 | 2012-01-19 | Wenying Chai | Piperazinyl derivatives useful as modulators of the neuropeptide y2 receptor |
| EP2303897A4 (en) * | 2008-06-05 | 2012-02-22 | Harvard College | HIGH VALENCIA PALLADIUM FLUORIDE COMPLEXES AND USES THEREOF |
| WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| US8324385B2 (en) | 2008-10-30 | 2012-12-04 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| WO2010059943A2 (en) | 2008-11-20 | 2010-05-27 | President And Fellows Of Harvard College | Fluorination of organic compounds |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| WO2011014520A2 (en) | 2009-07-29 | 2011-02-03 | Irm Llc | Compounds and compositions as modulators of gpr119 activity |
| ES2443016T3 (es) | 2009-08-26 | 2014-02-17 | Sanofi | Nuevos hidratos cristalinos de fluoroglicósidos heteroaromáticos, productos farmacéuticos que comprenden estos compuestos, y su empleo |
| JP2013507366A (ja) | 2009-10-09 | 2013-03-04 | アイアールエム・リミテッド・ライアビリティ・カンパニー | Gpr119活性モジュレーターとしての化合物および組成物 |
| US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| US8697739B2 (en) | 2010-07-29 | 2014-04-15 | Novartis Ag | Bicyclic acetyl-CoA carboxylase inhibitors and uses thereof |
| JP5941916B2 (ja) | 2010-09-22 | 2016-06-29 | アリーナ ファーマシューティカルズ, インコーポレイテッド | Gpr119レセプターのモジュレーターおよびそれに関連する障害の処置 |
| WO2012120055A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120053A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683698B1 (de) | 2011-03-08 | 2017-10-04 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683701B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| US8895547B2 (en) | 2011-03-08 | 2014-11-25 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| KR101326557B1 (ko) * | 2011-03-31 | 2013-11-08 | 주식회사종근당 | 카나비노이드 수용체〔cbi〕길항제로서의 벤즈아미드 유도체 |
| CN103596931B (zh) | 2011-04-12 | 2016-10-12 | 哈佛大学校长及研究员协会 | 有机化合物的氟化 |
| TW201311689A (zh) | 2011-08-05 | 2013-03-16 | 必治妥美雅史谷比公司 | 作為因子xia抑制劑之新穎巨環化合物 |
| US9067943B2 (en) * | 2011-11-25 | 2015-06-30 | Hoffmann-La Roche Inc. | [1,2,3]triazolo[4,5-D]pyrimidine derivatives |
| WO2014052622A1 (en) | 2012-09-26 | 2014-04-03 | President And Fellows Of Harvard College | Nickel fluorinating complexes and uses thereof |
| WO2014052619A1 (en) | 2012-09-27 | 2014-04-03 | Irm Llc | Piperidine derivatives and compositions as modulators of gpr119 activity |
| LT2964646T (lt) | 2013-03-07 | 2017-07-10 | F. Hoffmann-La Roche Ag | Nauji pirazolo dariniai |
| WO2014160668A1 (en) | 2013-03-25 | 2014-10-02 | Bristol-Myers Squibb Company | Tetrahydroisoquinolines containing substituted azoles as factor xia inhibitors |
| HRP20171099T1 (hr) | 2013-05-02 | 2017-10-06 | F. Hoffmann - La Roche Ag | Derivati pirolo[2,3-d]pirimidina kao agonisti cb2 receptora |
| PE20151977A1 (es) | 2013-05-02 | 2016-01-07 | Hoffmann La Roche | Nuevos derivados de purina |
| EP3943497A1 (en) | 2013-09-06 | 2022-01-26 | F. Hoffmann-La Roche AG | Triazolo[4,5-d]pyrimidine derivatives as cb2 receptor antagonists |
| US10759764B2 (en) | 2013-10-18 | 2020-09-01 | President And Fellows Of Harvard College | Fluorination of organic compounds |
| PL3242666T3 (pl) | 2015-01-06 | 2025-02-17 | Arena Pharmaceuticals, Inc. | Związek do zastosowania w leczeniu dolegliwości związanych z receptorem s1p1 |
| EP3294726A1 (en) | 2015-04-17 | 2018-03-21 | AbbVie Inc. | Indazolones as modulators of tnf signaling |
| AR104293A1 (es) | 2015-04-17 | 2017-07-12 | Abbvie Inc | Indazolonas como moduladores de la señalización de tnf |
| WO2016168641A1 (en) | 2015-04-17 | 2016-10-20 | Abbvie Inc. | Tricyclic modulators of tnf signaling |
| DK3310760T3 (da) | 2015-06-22 | 2022-10-24 | Arena Pharm Inc | Krystallinsk L-argininsalt af (R)-2-(7-(4-cyclopentyl-3-(trifluormethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3- yl)eddikesyre til anvendelse ved S1P1-receptor-associerede lidelser |
| WO2017012576A1 (en) * | 2015-07-23 | 2017-01-26 | Glaxosmithkline Intellectual Property Development Limited | Compounds |
| EP3471712B1 (en) * | 2016-06-20 | 2024-01-03 | The Regents of The University of Michigan | Small molecule inhibitors of aldh and uses thereof |
| WO2018013430A2 (en) | 2016-07-12 | 2018-01-18 | Arisan Therapeutics Inc. | Heterocyclic compounds for the treatment of arenavirus infection |
| WO2018049214A1 (en) | 2016-09-09 | 2018-03-15 | Incyte Corporation | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer |
| CN109923114B (zh) | 2016-09-09 | 2022-11-01 | 因赛特公司 | 作为hpk1调节剂的吡唑并吡啶衍生物和其用于治疗癌症的用途 |
| US20180072741A1 (en) | 2016-09-09 | 2018-03-15 | Incyte Corporation | Pyrazolopyrimidine compounds and uses thereof |
| CN106632069A (zh) * | 2016-11-18 | 2017-05-10 | 山东友帮生化科技有限公司 | 3‑氯‑6‑肼基哒嗪的合成方法 |
| WO2018152220A1 (en) | 2017-02-15 | 2018-08-23 | Incyte Corporation | Pyrazolopyridine compounds and uses thereof |
| CN110520124A (zh) | 2017-02-16 | 2019-11-29 | 艾尼纳制药公司 | 用于治疗原发性胆汁性胆管炎的化合物和方法 |
| US10722495B2 (en) | 2017-09-08 | 2020-07-28 | Incyte Corporation | Cyanoindazole compounds and uses thereof |
| AU2019223955B2 (en) | 2018-02-20 | 2024-06-13 | Incyte Corporation | N-(phenyl)-2-(phenyl)pyrimidine-4-carboxamide derivatives and related compounds as HPK1 inhibitors for treating cancer |
| US10745388B2 (en) | 2018-02-20 | 2020-08-18 | Incyte Corporation | Indazole compounds and uses thereof |
| US10752635B2 (en) | 2018-02-20 | 2020-08-25 | Incyte Corporation | Indazole compounds and uses thereof |
| US11299473B2 (en) | 2018-04-13 | 2022-04-12 | Incyte Corporation | Benzimidazole and indole compounds and uses thereof |
| BR112020024762A2 (pt) | 2018-06-06 | 2021-03-23 | Arena Pharmaceuticals, Inc. | métodos de tratamento de condições relacionadas ao receptor s1p1 |
| US10899755B2 (en) | 2018-08-08 | 2021-01-26 | Incyte Corporation | Benzothiazole compounds and uses thereof |
| US11111247B2 (en) | 2018-09-25 | 2021-09-07 | Incyte Corporation | Pyrazolopyrimidine compounds and uses thereof |
| US12419865B2 (en) | 2018-12-06 | 2025-09-23 | Arisan Therapeutics Inc. | Compounds for the treatment of arenavirus infection |
| WO2021026180A1 (en) | 2019-08-06 | 2021-02-11 | Incyte Corporation | Solid forms of an hpk1 inhibitor |
| EP4096661B1 (en) | 2020-01-29 | 2025-04-02 | Kamari Pharma Ltd. | Compounds and compositions for use in treating skin disorders |
| KR102584607B1 (ko) * | 2023-01-19 | 2023-10-04 | 아주대학교산학협력단 | 1h-피라졸-3-아마이드계 화합물 유도체를 포함하는 염증성 피부질환 예방 또는 치료용 조성물 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002026718A2 (en) * | 2000-09-29 | 2002-04-04 | Millennium Pharmaceutical, Inc. | Bicyclic pyrimidin-4-one based inhibitors of factor xa |
| WO2003104229A1 (ja) * | 2002-06-06 | 2003-12-18 | エーザイ株式会社 | 新規縮合イミダゾール誘導体 |
| WO2004087053A2 (en) * | 2003-03-25 | 2004-10-14 | Syrrx, Inc. | Dipeptidyl peptidase inhibitors |
| WO2005049613A1 (en) * | 2003-11-14 | 2005-06-02 | Merck Sharp & Dohme Limited | Bicyclic pyrimidin-4-(3h)-ones and analogues and derivatives thereof which modulate the function of the vanilloid-1 receptor (vr1) |
| CN101048408A (zh) * | 2004-10-26 | 2007-10-03 | Irm责任有限公司 | 作为大麻素受体1活性抑制剂的化合物和组合物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2631139B2 (ja) | 1988-10-06 | 1997-07-16 | ライオン株式会社 | 1H−ピラゾロ〔3,4−b〕ピラジン誘導体 |
| KR0151816B1 (ko) | 1994-02-08 | 1998-10-15 | 강박광 | 신규의 치환된 피리딜 이미다졸 유도체 및 그의 제조방법 |
| RU2272030C2 (ru) * | 2000-08-01 | 2006-03-20 | Оно Фармасьютикал Ко., Лтд. | Производные 3,4-дигидроизохинолина и фармацевтический агент, включающий его в качестве активного ингредиента |
| ATE375349T1 (de) * | 2002-08-02 | 2007-10-15 | Merck & Co Inc | Substituierte furo(2,3-b)pyridin derivate |
| AU2003301662A1 (en) | 2002-10-21 | 2004-05-13 | Bristol-Myers Squibb Company | Quinazolinones and derivatives thereof as factor xa inhibitors |
| US7129239B2 (en) | 2002-10-28 | 2006-10-31 | Pfizer Inc. | Purine compounds and uses thereof |
| US7141669B2 (en) | 2003-04-23 | 2006-11-28 | Pfizer Inc. | Cannabiniod receptor ligands and uses thereof |
| EP1620095A4 (en) * | 2003-04-24 | 2009-04-01 | Merck & Co Inc | HEMMER OF ACT ACTIVITY |
-
2005
- 2005-10-24 AR ARP050104440A patent/AR051596A1/es not_active Application Discontinuation
- 2005-10-25 PE PE2005001251A patent/PE20060599A1/es not_active Application Discontinuation
- 2005-10-25 TW TW094137369A patent/TW200630096A/zh unknown
- 2005-10-26 JP JP2007539039A patent/JP2008518016A/ja not_active Withdrawn
- 2005-10-26 CN CN2011101210450A patent/CN102241680A/zh active Pending
- 2005-10-26 BR BRPI0517015-0A patent/BRPI0517015A/pt not_active IP Right Cessation
- 2005-10-26 RU RU2007119449/04A patent/RU2431635C2/ru not_active IP Right Cessation
- 2005-10-26 EP EP05813001A patent/EP1807429A4/en not_active Withdrawn
- 2005-10-26 US US11/718,016 patent/US8158634B2/en not_active Expired - Fee Related
- 2005-10-26 AU AU2005299421A patent/AU2005299421B2/en not_active Ceased
- 2005-10-26 CA CA2581225A patent/CA2581225C/en not_active Expired - Fee Related
- 2005-10-26 WO PCT/US2005/038361 patent/WO2006047516A2/en not_active Ceased
- 2005-10-26 MX MX2007004936A patent/MX2007004936A/es not_active Application Discontinuation
- 2005-10-26 CN CN2005800368900A patent/CN101048408B/zh not_active Expired - Fee Related
- 2005-10-26 IN IN2514DEN2007 patent/IN2007DN02514A/en unknown
- 2005-10-26 CA CA2730374A patent/CA2730374A1/en not_active Abandoned
-
2007
- 2007-04-12 IL IL182527A patent/IL182527A0/en unknown
- 2007-04-18 MA MA29834A patent/MA28937B1/fr unknown
- 2007-04-25 KR KR1020077009370A patent/KR100919524B1/ko not_active Expired - Fee Related
- 2007-04-25 TN TNP2007000161A patent/TNSN07161A1/fr unknown
- 2007-04-26 EC EC2007007421A patent/ECSP077421A/es unknown
- 2007-05-07 NO NO20072352A patent/NO20072352L/no not_active Application Discontinuation
-
2009
- 2009-12-24 AU AU2009251216A patent/AU2009251216A1/en not_active Abandoned
-
2011
- 2011-06-22 JP JP2011138840A patent/JP2011190281A/ja active Pending
-
2012
- 2012-03-08 US US13/415,565 patent/US20120225869A1/en not_active Abandoned
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002026718A2 (en) * | 2000-09-29 | 2002-04-04 | Millennium Pharmaceutical, Inc. | Bicyclic pyrimidin-4-one based inhibitors of factor xa |
| WO2003104229A1 (ja) * | 2002-06-06 | 2003-12-18 | エーザイ株式会社 | 新規縮合イミダゾール誘導体 |
| WO2004087053A2 (en) * | 2003-03-25 | 2004-10-14 | Syrrx, Inc. | Dipeptidyl peptidase inhibitors |
| WO2005049613A1 (en) * | 2003-11-14 | 2005-06-02 | Merck Sharp & Dohme Limited | Bicyclic pyrimidin-4-(3h)-ones and analogues and derivatives thereof which modulate the function of the vanilloid-1 receptor (vr1) |
| CN101048408A (zh) * | 2004-10-26 | 2007-10-03 | Irm责任有限公司 | 作为大麻素受体1活性抑制剂的化合物和组合物 |
Non-Patent Citations (2)
| Title |
|---|
| F.OERTEL,等: "Synthese und Reaktionen substituierter Pyrazolo[3,4-d]pyrimidine", 《PHARMAZIE》 * |
| FLEMMING E.NIELSEN,等: "Phosphorus Pentoxide in Organic Synthesis. XV. A new synthesis of adenines from 4-acylamino-1H-imidazole-5-carbonitriles", 《CHEMICA SCRIPTA》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| NO20072352L (no) | 2007-05-31 |
| AR051596A1 (es) | 2007-01-24 |
| KR20070057980A (ko) | 2007-06-07 |
| WO2006047516A3 (en) | 2006-10-12 |
| AU2009251216A1 (en) | 2010-01-28 |
| KR100919524B1 (ko) | 2009-10-01 |
| ECSP077421A (es) | 2007-05-30 |
| RU2431635C2 (ru) | 2011-10-20 |
| MX2007004936A (es) | 2007-06-25 |
| BRPI0517015A (pt) | 2008-09-30 |
| CA2730374A1 (en) | 2006-05-04 |
| WO2006047516A2 (en) | 2006-05-04 |
| JP2011190281A (ja) | 2011-09-29 |
| IN2007DN02514A (enExample) | 2007-08-03 |
| JP2008518016A (ja) | 2008-05-29 |
| EP1807429A4 (en) | 2010-03-24 |
| TNSN07161A1 (en) | 2008-11-21 |
| AU2005299421A1 (en) | 2006-05-04 |
| TW200630096A (en) | 2006-09-01 |
| CN101048408B (zh) | 2011-07-06 |
| CA2581225C (en) | 2011-10-25 |
| IL182527A0 (en) | 2007-09-20 |
| AU2005299421B2 (en) | 2010-01-28 |
| US8158634B2 (en) | 2012-04-17 |
| PE20060599A1 (es) | 2006-08-22 |
| CA2581225A1 (en) | 2006-05-04 |
| MA28937B1 (fr) | 2007-10-01 |
| CN101048408A (zh) | 2007-10-03 |
| US20120225869A1 (en) | 2012-09-06 |
| EP1807429A2 (en) | 2007-07-18 |
| US20090247517A1 (en) | 2009-10-01 |
| RU2007119449A (ru) | 2008-12-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102241680A (zh) | 作为大麻素受体1活性抑制剂的化合物和组合物 | |
| JP5253374B2 (ja) | カンナビノイド受容体1活性の阻害剤としてのアゾロピリミジン類 | |
| CN104039784B (zh) | 取代的增环嘧啶及其用途 | |
| TWI572606B (zh) | 四氫吡唑并嘧啶化合物 | |
| CN103096718B (zh) | 可溶性鸟苷酸环化酶活化剂 | |
| EP1966215A1 (en) | Condensed heterocyclic compounds useful as dpp-iv inhibitors | |
| AU2004290643A1 (en) | 5,7-diaminopyrazolo [4,3-d] pyrimidines with PDE-5 inhibiting activity | |
| WO2002081474A1 (en) | Triazolophthalazine / quinoline / isoquinoline derivatives which are ligands for gaba-a receptors containing the alpha 5 subtype | |
| CN114728975A (zh) | 唑稠合的哒嗪-3(2h)-酮衍生物 | |
| EP1812112B1 (en) | Benzodiazepine derivatives as ROCK kinases inhibitors | |
| HK1122034B (en) | Azolopyrimidines as inhibitors of cannabinoid 1 activity |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20111116 |