EA014906B1 - 5-(арилсульфонил)пиразолопиперидины - Google Patents

Info

Publication number

EA014906B1

EA014906B1 EA200801481A EA200801481A EA014906B1 EA 014906 B1 EA014906 B1 EA 014906B1 EA 200801481 A EA200801481 A EA 200801481A EA 200801481 A EA200801481 A EA 200801481A EA 014906 B1 EA014906 B1 EA 014906B1

Authority

EA

Eurasian Patent Office

Prior art keywords

alkyl

compounds

formula

pyrazolo

chlorophenylsulfonyl

Prior art date

2005-12-01

Links

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• 150000001875 compounds Chemical class 0.000 claims abstract description 1045
• 238000000034 method Methods 0.000 claims abstract description 75
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 327
• 125000004076 pyridyl group Chemical group 0.000 claims description 318
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 317
• 229910052736 halogen Inorganic materials 0.000 claims description 290
• 150000002367 halogens Chemical class 0.000 claims description 282
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 279
• -1 phenyloxy Chemical group 0.000 claims description 245
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 187
• 125000000335 thiazolyl group Chemical group 0.000 claims description 164
• 125000002883 imidazolyl group Chemical group 0.000 claims description 151
• 229910052739 hydrogen Inorganic materials 0.000 claims description 140
• 239000000203 mixture Substances 0.000 claims description 101
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 97
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 94
• 229910052799 carbon Inorganic materials 0.000 claims description 88
• 125000002971 oxazolyl group Chemical group 0.000 claims description 67
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 64
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 64
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 62
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 61
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 54
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 54
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 53
• 125000001072 heteroaryl group Chemical group 0.000 claims description 50
• 125000003118 aryl group Chemical group 0.000 claims description 49
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 48
• 239000001257 hydrogen Substances 0.000 claims description 43
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 38
• 239000002904 solvent Substances 0.000 claims description 38
• 125000001188 haloalkyl group Chemical group 0.000 claims description 33
• 125000000217 alkyl group Chemical group 0.000 claims description 31
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 30
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 30
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 30
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 29
• 150000003839 salts Chemical class 0.000 claims description 29
• 125000001589 carboacyl group Chemical group 0.000 claims description 28
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
• 125000002757 morpholinyl group Chemical group 0.000 claims description 26
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 23
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 23
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 18
• 125000005843 halogen group Chemical group 0.000 claims description 18
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 17
• 125000001624 naphthyl group Chemical group 0.000 claims description 16
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 16
• 238000006467 substitution reaction Methods 0.000 claims description 15
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 14
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 14
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 13
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 13
• 125000001425 triazolyl group Chemical group 0.000 claims description 13
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 12
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 11
• 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
• 239000002671 adjuvant Substances 0.000 claims description 8
• 239000004305 biphenyl Substances 0.000 claims description 7
• TYZNGDLYLRYJCS-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-diethyl-4,6-dihydro-1h-pyrazolo[4,3-c]pyridin-7-one Chemical compound CCC1C(=O)C=2NN=CC=2C(CC)N1S(=O)(=O)C1=CC=C(Cl)C=C1 TYZNGDLYLRYJCS-UHFFFAOYSA-N 0.000 claims description 6
• 235000010290 biphenyl Nutrition 0.000 claims description 6
• 125000006267 biphenyl group Chemical group 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• SELYJABLPLKXOY-UHFFFAOYSA-N methyl n,n-dimethylcarbamate Chemical compound COC(=O)N(C)C SELYJABLPLKXOY-UHFFFAOYSA-N 0.000 claims description 6
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 5
• SHPWXEFRRYKBDM-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-6-phenyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C=2C=CC=CC=2)CC2=NNC=C2C1 SHPWXEFRRYKBDM-UHFFFAOYSA-N 0.000 claims description 5
• 239000011230 binding agent Substances 0.000 claims description 5
• 125000005842 heteroatom Chemical group 0.000 claims description 5
• ABPUPKAKVGTPJW-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-6-(3,5-difluorophenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound FC1=CC(F)=CC(C2N(CC=3C=NNC=3C2)S(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 ABPUPKAKVGTPJW-UHFFFAOYSA-N 0.000 claims description 4
• ZRCZGEIHIFDAPM-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(4-chlorophenyl)sulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1N(S(=O)(=O)C=2C=CC(Cl)=CC=2)CC(C=NN2)=C2C1 ZRCZGEIHIFDAPM-UHFFFAOYSA-N 0.000 claims description 4
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
• 239000007884 disintegrant Substances 0.000 claims description 4
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 3
• FNVZIUZHHCMTFP-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(4-chlorophenyl)sulfonyl-6-ethyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound CCC1CC2=NNC=C2C(C=2C=CC(Cl)=CC=2)N1S(=O)(=O)C1=CC=C(Cl)C=C1 FNVZIUZHHCMTFP-UHFFFAOYSA-N 0.000 claims description 3
• INFDFYKJYGGPKY-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4-pyrimidin-5-yl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C=2C=NC=NC=2)C(C=NN2)=C2CC1 INFDFYKJYGGPKY-UHFFFAOYSA-N 0.000 claims description 3
• QZITUMLLZQLARP-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-6-(4-fluorophenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound C1=CC(F)=CC=C1C1N(S(=O)(=O)C=2C=CC(Cl)=CC=2)CC(C=NN2)=C2C1 QZITUMLLZQLARP-UHFFFAOYSA-N 0.000 claims description 3
• BVXHINMPEZLERH-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-6-propan-2-yl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound CC(C)C1CC=2NN=CC=2CN1S(=O)(=O)C1=CC=C(Cl)C=C1 BVXHINMPEZLERH-UHFFFAOYSA-N 0.000 claims description 3
• DHZZUOUZBFLGOY-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-6-pyrimidin-5-yl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C=2C=NC=NC=2)CC(NN=C2)=C2C1 DHZZUOUZBFLGOY-UHFFFAOYSA-N 0.000 claims description 3
• NLFUWFNEKPIFHZ-UHFFFAOYSA-N 6-benzyl-5-(4-chlorophenyl)sulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(CC=2C=CC=CC=2)CC(NN=C2)=C2C1 NLFUWFNEKPIFHZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 3
• GIDRPZDBBKBMNK-UHFFFAOYSA-N 1-[4-acetyl-5-(4-chlorophenyl)sulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-6-yl]ethanone Chemical compound CC(=O)C1CC=2NN=CC=2C(C(C)=O)N1S(=O)(=O)C1=CC=C(Cl)C=C1 GIDRPZDBBKBMNK-UHFFFAOYSA-N 0.000 claims description 2
• OGBXQEIQBNWCPQ-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)sulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-4-yl]-1,3-thiazole Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C=2SC=CN=2)C(C=NN2)=C2CC1 OGBXQEIQBNWCPQ-UHFFFAOYSA-N 0.000 claims description 2
• ICLCLISNCTWXGA-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)sulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-6-yl]-1,3-thiazole Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C=2SC=CN=2)CC(NN=C2)=C2C1 ICLCLISNCTWXGA-UHFFFAOYSA-N 0.000 claims description 2
• HAQUEDTVQZIXFB-UHFFFAOYSA-N 4-(1h-benzimidazol-2-yl)-5-(4-chlorophenyl)sulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C=2NC3=CC=CC=C3N=2)C2=CNN=C2CC1 HAQUEDTVQZIXFB-UHFFFAOYSA-N 0.000 claims description 2
• DFAPLCUDTXZPSZ-UHFFFAOYSA-N 4-pyrimidin-5-yl-5-[4-(trifluoromethyl)phenyl]sulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound C1=CC(C(F)(F)F)=CC=C1S(=O)(=O)N1C(C=2C=NC=NC=2)C(C=NN2)=C2CC1 DFAPLCUDTXZPSZ-UHFFFAOYSA-N 0.000 claims description 2
• FWFPFPVMQRARFK-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-bis(1,1-difluoroethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound CC(F)(F)C1CC=2NN=CC=2C(C(C)(F)F)N1S(=O)(=O)C1=CC=C(Cl)C=C1 FWFPFPVMQRARFK-UHFFFAOYSA-N 0.000 claims description 2
• IJKKVNQKLIUEKZ-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-bis(2,2,2-trifluoroethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound FC(F)(F)CC1CC=2NN=CC=2C(CC(F)(F)F)N1S(=O)(=O)C1=CC=C(Cl)C=C1 IJKKVNQKLIUEKZ-UHFFFAOYSA-N 0.000 claims description 2
• VQICZUMHISWBRF-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-bis(2,2-difluoroethenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound FC(F)=CC1CC=2NN=CC=2C(C=C(F)F)N1S(=O)(=O)C1=CC=C(Cl)C=C1 VQICZUMHISWBRF-UHFFFAOYSA-N 0.000 claims description 2
• LPOKCOBIKCGVBE-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-bis(2,2-difluoroethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound FC(F)CC1CC=2NN=CC=2C(CC(F)F)N1S(=O)(=O)C1=CC=C(Cl)C=C1 LPOKCOBIKCGVBE-UHFFFAOYSA-N 0.000 claims description 2
• JGAFDAJFEDNFIR-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-bis(difluoromethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound FC(F)C1CC=2NN=CC=2C(C(F)F)N1S(=O)(=O)C1=CC=C(Cl)C=C1 JGAFDAJFEDNFIR-UHFFFAOYSA-N 0.000 claims description 2
• FTXBIZQXDZLQIN-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-bis(fluoromethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound FCC1CC=2NN=CC=2C(CF)N1S(=O)(=O)C1=CC=C(Cl)C=C1 FTXBIZQXDZLQIN-UHFFFAOYSA-N 0.000 claims description 2
• VCFVIFBFKJBPAG-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-bis(trifluoromethoxymethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound FC(F)(F)OCC1CC=2NN=CC=2C(COC(F)(F)F)N1S(=O)(=O)C1=CC=C(Cl)C=C1 VCFVIFBFKJBPAG-UHFFFAOYSA-N 0.000 claims description 2
• TVGCMTFAICEQPV-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-bis(trifluoromethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound FC(F)(F)C1CC=2NN=CC=2C(C(F)(F)F)N1S(=O)(=O)C1=CC=C(Cl)C=C1 TVGCMTFAICEQPV-UHFFFAOYSA-N 0.000 claims description 2
• LDJVTIWSHGAJBZ-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-bis[difluoro(methoxy)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound COC(F)(F)C1CC=2NN=CC=2C(C(F)(F)OC)N1S(=O)(=O)C1=CC=C(Cl)C=C1 LDJVTIWSHGAJBZ-UHFFFAOYSA-N 0.000 claims description 2
• MGBJJPSCKFZVTC-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-di(propan-2-yl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound CC(C)C1CC=2NN=CC=2C(C(C)C)N1S(=O)(=O)C1=CC=C(Cl)C=C1 MGBJJPSCKFZVTC-UHFFFAOYSA-N 0.000 claims description 2
• MQMZGGJQWVAGCT-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-dicyclopropyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C2CC2)C(C=NN2)=C2CC1C1CC1 MQMZGGJQWVAGCT-UHFFFAOYSA-N 0.000 claims description 2
• QTNJCLYRWVYMLP-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-diethyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-7-amine Chemical compound CCC1C(N)C=2NN=CC=2C(CC)N1S(=O)(=O)C1=CC=C(Cl)C=C1 QTNJCLYRWVYMLP-UHFFFAOYSA-N 0.000 claims description 2
• BIOZVVKTOIIOJB-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-diethyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-7-ol Chemical compound CCC1C(O)C=2NN=CC=2C(CC)N1S(=O)(=O)C1=CC=C(Cl)C=C1 BIOZVVKTOIIOJB-UHFFFAOYSA-N 0.000 claims description 2
• LBUIKNKQOBTCII-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-diethyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound CCC1CC=2NN=CC=2C(CC)N1S(=O)(=O)C1=CC=C(Cl)C=C1 LBUIKNKQOBTCII-UHFFFAOYSA-N 0.000 claims description 2
• UYXLRRKFIURBQN-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-diethyl-7,7-difluoro-4,6-dihydro-1h-pyrazolo[4,3-c]pyridine Chemical compound CCC1C(F)(F)C=2NN=CC=2C(CC)N1S(=O)(=O)C1=CC=C(Cl)C=C1 UYXLRRKFIURBQN-UHFFFAOYSA-N 0.000 claims description 2
• VUOTZLZWRQAMKT-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-diethyl-7-fluoro-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound CCC1C(F)C=2NN=CC=2C(CC)N1S(=O)(=O)C1=CC=C(Cl)C=C1 VUOTZLZWRQAMKT-UHFFFAOYSA-N 0.000 claims description 2
• VSORWHCBJZKYIQ-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4,6-dimethyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound CC1CC=2NN=CC=2C(C)N1S(=O)(=O)C1=CC=C(Cl)C=C1 VSORWHCBJZKYIQ-UHFFFAOYSA-N 0.000 claims description 2
• NEUBWALUOOQMFO-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4-propan-2-yl-4,6-dihydro-1h-pyrazolo[4,3-c]pyridin-7-one Chemical compound C1C(=O)C=2NN=CC=2C(C(C)C)N1S(=O)(=O)C1=CC=C(Cl)C=C1 NEUBWALUOOQMFO-UHFFFAOYSA-N 0.000 claims description 2
• PJWCXGDPACNDRU-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-4-pyrimidin-5-yl-4,6-dihydro-1h-pyrazolo[4,3-c]pyridin-7-one Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C=2C=NC=NC=2)C(C=NN2)=C2C(=O)C1 PJWCXGDPACNDRU-UHFFFAOYSA-N 0.000 claims description 2
• XDWSGTXQGWIEGP-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-6-cyclopropyl-4-pyrimidin-5-yl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C=2C=NC=NC=2)C(C=NN2)=C2CC1C1CC1 XDWSGTXQGWIEGP-UHFFFAOYSA-N 0.000 claims description 2
• GURVCFNDFPUXLC-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-6-cyclopropyl-6,7-dihydro-1h-pyrazolo[4,3-c]pyridin-4-one Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(=O)C(C=NN2)=C2CC1C1CC1 GURVCFNDFPUXLC-UHFFFAOYSA-N 0.000 claims description 2
• XYGOBGUUUWYZHO-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-6-ethyl-6,7-dihydro-1h-pyrazolo[4,3-c]pyridin-4-one Chemical compound CCC1CC=2NN=CC=2C(=O)N1S(=O)(=O)C1=CC=C(Cl)C=C1 XYGOBGUUUWYZHO-UHFFFAOYSA-N 0.000 claims description 2
• TWLIVHHOFPVVPT-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-6-methyl-4-pyrimidin-5-yl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound CC1CC=2NN=CC=2C(C=2C=NC=NC=2)N1S(=O)(=O)C1=CC=C(Cl)C=C1 TWLIVHHOFPVVPT-UHFFFAOYSA-N 0.000 claims description 2
• ZSFBCSDOPXBMHO-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-6-pyridin-3-yl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C=2C=NC=CC=2)CC(NN=C2)=C2C1 ZSFBCSDOPXBMHO-UHFFFAOYSA-N 0.000 claims description 2
• FQMAGFMWKDKHCK-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-6-pyridin-4-yl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C=2C=CN=CC=2)CC(NN=C2)=C2C1 FQMAGFMWKDKHCK-UHFFFAOYSA-N 0.000 claims description 2
• BLXAFOWVHKZTSV-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-6-pyrimidin-5-yl-4,6-dihydro-1h-pyrazolo[4,3-c]pyridin-7-one Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C=2C=NC=NC=2)C(=O)C(NN=C2)=C2C1 BLXAFOWVHKZTSV-UHFFFAOYSA-N 0.000 claims description 2
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