CA2581225C - Compounds and compositions as inhibitors of cannabinoid receptor 1 activity - Google Patents

Info

Publication number

CA2581225C

CA2581225C CA2581225A CA2581225A CA2581225C CA 2581225 C CA2581225 C CA 2581225C CA 2581225 A CA2581225 A CA 2581225A CA 2581225 A CA2581225 A CA 2581225A CA 2581225 C CA2581225 C CA 2581225C

Authority

CA

Canada

Prior art keywords

phenyl

dihydro

pyrazolo

pyrimidin

chloro

Prior art date

2004-10-26

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 338
• 239000000203 mixture Substances 0.000 title claims description 137
• 230000000694 effects Effects 0.000 title abstract description 18
• 102100033868 Cannabinoid receptor 1 Human genes 0.000 title abstract description 5
• 101710187010 Cannabinoid receptor 1 Proteins 0.000 title abstract description 5
• 239000003112 inhibitor Substances 0.000 title description 21
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 54
• 201000010099 disease Diseases 0.000 claims abstract description 31
• 208000035475 disorder Diseases 0.000 claims abstract description 17
• -1 C3-12cyclolalkyl Chemical group 0.000 claims description 247
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 119
• 229910052739 hydrogen Inorganic materials 0.000 claims description 83
• 150000003254 radicals Chemical class 0.000 claims description 77
• 125000005843 halogen group Chemical group 0.000 claims description 69
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 58
• 239000001257 hydrogen Substances 0.000 claims description 57
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 54
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 52
• 150000003839 salts Chemical class 0.000 claims description 50
• 150000002431 hydrogen Chemical group 0.000 claims description 49
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 43
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 43
• 229910052757 nitrogen Inorganic materials 0.000 claims description 41
• 125000001072 heteroaryl group Chemical group 0.000 claims description 37
• 238000011282 treatment Methods 0.000 claims description 34
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• 239000012453 solvate Substances 0.000 claims description 29
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 28
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 25
• 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 25
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 24
• 125000000882 C2-C6 alkenyl group Chemical class 0.000 claims description 24
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 24
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 22
• 208000008589 Obesity Diseases 0.000 claims description 21
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 21
• 235000020824 obesity Nutrition 0.000 claims description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• 230000001404 mediated effect Effects 0.000 claims description 20
• 125000004076 pyridyl group Chemical group 0.000 claims description 20
• 125000006652 (C3-C12) cycloalkyl group Chemical class 0.000 claims description 19
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 17
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 17
• 125000004193 piperazinyl group Chemical group 0.000 claims description 17
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 17
• 235000012631 food intake Nutrition 0.000 claims description 16
• 125000002541 furyl group Chemical group 0.000 claims description 16
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 16
• 208000030159 metabolic disease Diseases 0.000 claims description 15
• 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 15
• 235000014632 disordered eating Nutrition 0.000 claims description 14
• 125000003118 aryl group Chemical group 0.000 claims description 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 125000001246 bromo group Chemical group Br* 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• 230000037406 food intake Effects 0.000 claims description 12
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 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 9
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• 230000037396 body weight Effects 0.000 claims description 9
• 125000001153 fluoro group Chemical group F* 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000003386 piperidinyl group Chemical group 0.000 claims description 9
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 9
• 208000030814 Eating disease Diseases 0.000 claims description 8
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 8
• 206010019196 Head injury Diseases 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 8
• 230000002490 cerebral effect Effects 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
• COTQVJQUIDYXSZ-UHFFFAOYSA-N 6-(4-bromophenyl)-5-(4-chlorophenyl)-4-oxo-1-phenylpyrazolo[3,4-d]pyrimidine-3-carboxylic acid Chemical compound C1=2N=C(C=3C=CC(Br)=CC=3)N(C=3C=CC(Cl)=CC=3)C(=O)C=2C(C(=O)O)=NN1C1=CC=CC=C1 COTQVJQUIDYXSZ-UHFFFAOYSA-N 0.000 claims description 7
• 208000006673 asthma Diseases 0.000 claims description 7
• 208000010877 cognitive disease Diseases 0.000 claims description 7
• JQDKZDULLRGNAR-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-1-(2-nitrophenyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound [O-][N+](=O)C1=CC=CC=C1N1C(N=C(C=2C(=CC(Cl)=CC=2)Cl)N(C=2C=CC(Cl)=CC=2)C2=O)=C2C=N1 JQDKZDULLRGNAR-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• 206010006550 Bulimia nervosa Diseases 0.000 claims description 6
• 208000010235 Food Addiction Diseases 0.000 claims description 6
• 206010020772 Hypertension Diseases 0.000 claims description 6
• 208000026139 Memory disease Diseases 0.000 claims description 6
• 208000028017 Psychotic disease Diseases 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• 125000002346 iodo group Chemical group I* 0.000 claims description 6
• 230000005980 lung dysfunction Effects 0.000 claims description 6
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
• 201000009032 substance abuse Diseases 0.000 claims description 6
• 231100000736 substance abuse Toxicity 0.000 claims description 6
• 208000011117 substance-related disease Diseases 0.000 claims description 6
• COEHPBLCHQVRQQ-UHFFFAOYSA-N 1-(4-aminophenyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(N)=CC=C1N1C(N=C(C=2C(=CC(Cl)=CC=2)Cl)N(C=2C=CC(Cl)=CC=2)C2=O)=C2C=N1 COEHPBLCHQVRQQ-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• HIGVSHPEZWKCJI-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-[4-(2-chloropyrimidin-4-yl)phenyl]-3-methylsulfanyl-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(SC)=NN1C1=CC=CC=C1 HIGVSHPEZWKCJI-UHFFFAOYSA-N 0.000 claims description 5
• 208000019901 Anxiety disease Diseases 0.000 claims description 5
• 208000019695 Migraine disease Diseases 0.000 claims description 5
• 208000018737 Parkinson disease Diseases 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 230000000747 cardiac effect Effects 0.000 claims description 5
• 230000004064 dysfunction Effects 0.000 claims description 5
• 206010015037 epilepsy Diseases 0.000 claims description 5
• DRAGIKIPAJKHMR-UHFFFAOYSA-N ethyl 6-(4-bromophenyl)-5-(4-chlorophenyl)-4-oxo-1-phenylpyrazolo[3,4-d]pyrimidine-3-carboxylate Chemical compound C1=2N=C(C=3C=CC(Br)=CC=3)N(C=3C=CC(Cl)=CC=3)C(=O)C=2C(C(=O)OCC)=NN1C1=CC=CC=C1 DRAGIKIPAJKHMR-UHFFFAOYSA-N 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
• XPTSYTNDFCYKPW-UHFFFAOYSA-N methyl 4-[5-(4-chlorophenyl)-4-oxo-1-phenylpyrazolo[3,4-d]pyrimidin-6-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 XPTSYTNDFCYKPW-UHFFFAOYSA-N 0.000 claims description 5
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 5
• 206010027599 migraine Diseases 0.000 claims description 5
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
• 201000001119 neuropathy Diseases 0.000 claims description 5
• 230000007823 neuropathy Effects 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 5
• 230000002265 prevention Effects 0.000 claims description 5
• 208000020016 psychiatric disease Diseases 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 201000000980 schizophrenia Diseases 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 230000002792 vascular Effects 0.000 claims description 5
• QXJDCZLYWONAIA-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-4-oxo-1-phenylpyrazolo[3,4-d]pyrimidin-6-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C(N(C1=O)C=2C=CC(Cl)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 QXJDCZLYWONAIA-UHFFFAOYSA-N 0.000 claims description 4
• QADRWQDDMAOCAU-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-4-oxopyrazolo[3,4-d]pyrimidin-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1C(N=C(C=2C(=CC(Cl)=CC=2)Cl)N(C=2C=CC(Cl)=CC=2)C2=O)=C2C=N1 QADRWQDDMAOCAU-UHFFFAOYSA-N 0.000 claims description 4
• MJHKIDXPBNVAGM-UHFFFAOYSA-N 5,6-bis(3-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 MJHKIDXPBNVAGM-UHFFFAOYSA-N 0.000 claims description 4
• YPGHVKQSXGSYKD-UHFFFAOYSA-N 5-(4-bromophenyl)-6-(2-fluorophenyl)-1-(thian-4-yl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1C=NN2C1CCSCC1 YPGHVKQSXGSYKD-UHFFFAOYSA-N 0.000 claims description 4
• 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 claims description 4
• JYFSAXZZRGLODI-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-1-(4-nitrophenyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1C(N=C(C=2C(=CC(Cl)=CC=2)Cl)N(C=2C=CC(Cl)=CC=2)C2=O)=C2C=N1 JYFSAXZZRGLODI-UHFFFAOYSA-N 0.000 claims description 4
• NXLRRIHWXSLCOD-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-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(Cl)C=C1Cl NXLRRIHWXSLCOD-UHFFFAOYSA-N 0.000 claims description 4
• 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 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
• 208000000044 Amnesia Diseases 0.000 claims description 4
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
• 208000035895 Guillain-Barré syndrome Diseases 0.000 claims description 4
• 208000001953 Hypotension Diseases 0.000 claims description 4
• 206010049567 Miller Fisher syndrome Diseases 0.000 claims description 4
• 125000006226 butoxyethyl group Chemical group 0.000 claims description 4
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 4
• 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 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• DWABZAHOZRKJRF-UHFFFAOYSA-N ethyl 5-(4-chlorophenyl)-4-oxo-1-phenyl-6-(4-phenylphenyl)pyrazolo[3,4-d]pyrimidine-3-carboxylate Chemical compound C1=2N=C(C=3C=CC(=CC=3)C=3C=CC=CC=3)N(C=3C=CC(Cl)=CC=3)C(=O)C=2C(C(=O)OCC)=NN1C1=CC=CC=C1 DWABZAHOZRKJRF-UHFFFAOYSA-N 0.000 claims description 4
• 125000001041 indolyl group Chemical group 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
• 206010027175 memory impairment Diseases 0.000 claims description 4
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 4
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
• 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• 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 claims description 3
• HLYRSBSWPJDADE-UHFFFAOYSA-N 5,6-bis(2-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC=C1C(N(C1=O)C=2C(=CC=CC=2)C)=NC2=C1C=NN2C1=CC=CC=C1 HLYRSBSWPJDADE-UHFFFAOYSA-N 0.000 claims description 3
• GDHPGXMZIAFXCN-UHFFFAOYSA-N 5,6-bis(4-bromophenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Br)=CC=C1C(N(C1=O)C=2C=CC(Br)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 GDHPGXMZIAFXCN-UHFFFAOYSA-N 0.000 claims description 3
• IIQWUHIWAXFABY-UHFFFAOYSA-N 5,6-bis(4-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C)=CC=C1C(N(C1=O)C=2C=CC(C)=CC=2)=NC2=C1C=NN2C1=CC=CC=C1 IIQWUHIWAXFABY-UHFFFAOYSA-N 0.000 claims description 3
• BUSHPLPJLFMRIS-UHFFFAOYSA-N 5-(2-methylphenyl)-1,6-diphenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C(C=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=CC=C1 BUSHPLPJLFMRIS-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
• GJTYAKKSVFSNAE-UHFFFAOYSA-N 5-(3,5-dimethylphenyl)-6-(3-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=C(C)C=C(C)C=2)=C1 GJTYAKKSVFSNAE-UHFFFAOYSA-N 0.000 claims description 3
• WPYGRQTXWXUSEV-UHFFFAOYSA-N 5-(3-chlorophenyl)-1,6-diphenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound ClC1=CC=CC(N2C(C=3C=NN(C=3N=C2C=2C=CC=CC=2)C=2C=CC=CC=2)=O)=C1 WPYGRQTXWXUSEV-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
• AROPKPIERSUSNA-UHFFFAOYSA-N 5-(3-chlorophenyl)-6-(3-methylphenyl)-1-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC(C=2N(C(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)C=2C=C(Cl)C=CC=2)=C1 AROPKPIERSUSNA-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
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• UHAQKBKDJDVJBQ-UHFFFAOYSA-N 6-(4-bromophenyl)-5-(4-chlorophenyl)-1-phenyl-3-(piperidine-1-carbonyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C(C(=O)N2CCCCC2)=NN2C=3C=CC=CC=3)=C2N=C1C1=CC=C(Br)C=C1 UHAQKBKDJDVJBQ-UHFFFAOYSA-N 0.000 claims description 2
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• 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
• LFZFYWTYFLPNNK-UHFFFAOYSA-N 6-[4-(2-aminopyrimidin-4-yl)phenyl]-5-(4-chlorophenyl)-4-oxo-1-phenylpyrazolo[3,4-d]pyrimidine-3-carboxamide 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(C(=O)N)=NN1C1=CC=CC=C1 LFZFYWTYFLPNNK-UHFFFAOYSA-N 0.000 claims description 2
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• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
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