CA2632227A1 - 5-(arylsulfonyl)-pyrazolopiperidines - Google Patents
5-(arylsulfonyl)-pyrazolopiperidines Download PDFInfo
- Publication number
- CA2632227A1 CA2632227A1 CA002632227A CA2632227A CA2632227A1 CA 2632227 A1 CA2632227 A1 CA 2632227A1 CA 002632227 A CA002632227 A CA 002632227A CA 2632227 A CA2632227 A CA 2632227A CA 2632227 A1 CA2632227 A1 CA 2632227A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- formula
- compounds
- pyrazolo
- methyl
- 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.)
- Abandoned
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- 150000001875 compounds Chemical class 0.000 claims abstract description 1027
- 238000000034 method Methods 0.000 claims abstract description 80
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 35
- -1 C0-C3alkyl-C(O)OR' Chemical group 0.000 claims description 420
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 331
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 321
- 125000004076 pyridyl group Chemical group 0.000 claims description 312
- 125000000217 alkyl group Chemical group 0.000 claims description 301
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 274
- 229910052736 halogen Inorganic materials 0.000 claims description 181
- 150000002367 halogens Chemical class 0.000 claims description 180
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 176
- 125000000335 thiazolyl group Chemical group 0.000 claims description 141
- 125000003545 alkoxy group Chemical group 0.000 claims description 135
- 125000002883 imidazolyl group Chemical group 0.000 claims description 125
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 102
- 125000005843 halogen group Chemical group 0.000 claims description 101
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 99
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 79
- 229910052739 hydrogen Inorganic materials 0.000 claims description 79
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 72
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 63
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 63
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 63
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 61
- 125000002971 oxazolyl group Chemical group 0.000 claims description 58
- 125000001188 haloalkyl group Chemical group 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 56
- 125000001072 heteroaryl group Chemical group 0.000 claims description 54
- 125000003282 alkyl amino group Chemical group 0.000 claims description 52
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 52
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 49
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 47
- 125000001589 carboacyl group Chemical group 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 37
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 35
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 32
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 29
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 29
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 28
- 125000001544 thienyl group Chemical group 0.000 claims description 27
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 25
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 24
- 125000002757 morpholinyl group Chemical group 0.000 claims description 23
- 125000004193 piperazinyl group Chemical group 0.000 claims description 20
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 17
- 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 15
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 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
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 13
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 13
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 13
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 11
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 11
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 11
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 11
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 11
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 125000001425 triazolyl group Chemical group 0.000 claims description 10
- 239000002671 adjuvant Substances 0.000 claims description 9
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
- 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 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- NYQCPQYGVZNKQO-UHFFFAOYSA-N 4,6-diethyl-5-pyridin-2-ylsulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound CCC1CC2=NNC=C2C(CC)N1S(=O)(=O)C1=CC=CC=N1 NYQCPQYGVZNKQO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 239000007884 disintegrant Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- MXCHFWLKPVDOPC-UHFFFAOYSA-N 4,6-dimethyl-5-[4-(trifluoromethyl)phenyl]sulfonyl-4,6-dihydro-1h-pyrazolo[4,3-c]pyridin-7-one Chemical compound CC1C(=O)C2=NNC=C2C(C)N1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 MXCHFWLKPVDOPC-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- SELYJABLPLKXOY-UHFFFAOYSA-N methyl n,n-dimethylcarbamate Chemical compound COC(=O)N(C)C SELYJABLPLKXOY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-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
- CMEPURNZGZVVGK-UHFFFAOYSA-N 4,6-dimethyl-5-pyridin-2-ylsulfonyl-4,6-dihydro-1h-pyrazolo[4,3-c]pyridin-7-one Chemical compound CC1C(=O)C=2NN=CC=2C(C)N1S(=O)(=O)C1=CC=CC=N1 CMEPURNZGZVVGK-UHFFFAOYSA-N 0.000 claims description 2
- LEIFEKVLPCZEMT-UHFFFAOYSA-N 4-(1h-imidazol-2-yl)-6-methyl-5-[4-(trifluoromethyl)phenyl]sulfonyl-4,6-dihydro-1h-pyrazolo[4,3-c]pyridin-7-one Chemical compound C1=2C=NNC=2C(=O)C(C)N(S(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)C1C1=NC=CN1 LEIFEKVLPCZEMT-UHFFFAOYSA-N 0.000 claims description 2
- PVNUMKBZVPYVGW-UHFFFAOYSA-N 4-(1h-imidazol-5-yl)-6-methyl-5-[4-(trifluoromethyl)phenyl]sulfonyl-4,6-dihydro-1h-pyrazolo[4,3-c]pyridin-7-one Chemical compound C1=2C=NNC=2C(=O)C(C)N(S(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)C1C1=CN=CN1 PVNUMKBZVPYVGW-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
- 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
- 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
- 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
- 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
- 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
- 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 2
- 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 2
- 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 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
- 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 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
- 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 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
- PSBVASZJNLJDAQ-UHFFFAOYSA-N 5-(4-fluorophenyl)sulfonyl-4,6-dimethyl-4,6-dihydro-1h-pyrazolo[4,3-c]pyridin-7-one Chemical compound CC1C(=O)C=2NN=CC=2C(C)N1S(=O)(=O)C1=CC=C(F)C=C1 PSBVASZJNLJDAQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- PUBWZOHDDYWHMC-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(4-chlorophenyl)sulfonyl-4-ethyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound C1C=2NN=CC=2C(CC)N(S(=O)(=O)C=2C=CC(Cl)=CC=2)C1C1=CC=C(Cl)C=C1 PUBWZOHDDYWHMC-UHFFFAOYSA-N 0.000 claims description 2
- NYKKLADUPJMJDI-UHFFFAOYSA-N 6-methyl-4-(1,3-thiazol-2-yl)-5-[4-(trifluoromethyl)phenyl]sulfonyl-4,6-dihydro-1h-pyrazolo[4,3-c]pyridin-7-one Chemical compound C1=2C=NNC=2C(=O)C(C)N(S(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)C1C1=NC=CS1 NYKKLADUPJMJDI-UHFFFAOYSA-N 0.000 claims description 2
- OSXXSBWDLVDOPD-UHFFFAOYSA-N 6-methyl-4-pyridin-3-yl-5-[4-(trifluoromethyl)phenyl]sulfonyl-4,6-dihydro-1h-pyrazolo[4,3-c]pyridin-7-one Chemical compound C1=2C=NNC=2C(=O)C(C)N(S(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)C1C1=CC=CN=C1 OSXXSBWDLVDOPD-UHFFFAOYSA-N 0.000 claims description 2
- MGPOXPHMAOQZOW-UHFFFAOYSA-N 6-methyl-4-pyridin-4-yl-5-[4-(trifluoromethyl)phenyl]sulfonyl-4,6-dihydro-1h-pyrazolo[4,3-c]pyridin-7-one Chemical compound C1=2C=NNC=2C(=O)C(C)N(S(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)C1C1=CC=NC=C1 MGPOXPHMAOQZOW-UHFFFAOYSA-N 0.000 claims description 2
- NBQFIIANGXHOLA-UHFFFAOYSA-N 6-methyl-4-pyrimidin-5-yl-5-[4-(trifluoromethyl)phenyl]sulfonyl-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(C(F)(F)F)C=C1 NBQFIIANGXHOLA-UHFFFAOYSA-N 0.000 claims description 2
- JSMZYVDGBUGFNA-UHFFFAOYSA-N N-[5-(4-chlorophenyl)sulfonyl-4,6-diethyl-4,6-dihydro-1H-pyrazolo[4,3-c]pyridin-7-ylidene]hydroxylamine Chemical compound CCC1C(=NO)C=2NN=CC=2C(CC)N1S(=O)(=O)C1=CC=C(Cl)C=C1 JSMZYVDGBUGFNA-UHFFFAOYSA-N 0.000 claims description 2
- PXZHQXQGCCNTBI-UHFFFAOYSA-N [5-(4-chlorophenyl)sulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-4-yl]methyl n,n-dimethylcarbamate Chemical compound C1CC=2NN=CC=2C(COC(=O)N(C)C)N1S(=O)(=O)C1=CC=C(Cl)C=C1 PXZHQXQGCCNTBI-UHFFFAOYSA-N 0.000 claims description 2
- UJMLISCWFCEOJY-UHFFFAOYSA-N [5-(4-chlorophenyl)sulfonyl-1-(dimethylcarbamoyl)-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-4-yl]methyl n,n-dimethylcarbamate Chemical compound C1CC(N(N=C2)C(=O)N(C)C)=C2C(COC(=O)N(C)C)N1S(=O)(=O)C1=CC=C(Cl)C=C1 UJMLISCWFCEOJY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 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 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 239000008251 pharmaceutical emulsion Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000008300 phosphoramidites Chemical class 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
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- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 201000002212 progressive supranuclear palsy Diseases 0.000 description 1
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004590 pyridopyridyl group Chemical group N1=C(C=CC2=C1C=CC=N2)* 0.000 description 1
- FREJAOSUHFGDBW-UHFFFAOYSA-N pyrimidine-5-carbaldehyde Chemical compound O=CC1=CN=CN=C1 FREJAOSUHFGDBW-UHFFFAOYSA-N 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000004620 quinolinyl-N-oxide group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 230000011218 segmentation Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 210000002023 somite Anatomy 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000012128 staining reagent Substances 0.000 description 1
- 230000004960 subcellular localization Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- ZZIKGBYOHWQFFK-UHFFFAOYSA-N tert-butyl 5-(hydroxymethylidene)-4-oxo-2-phenylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC(=CO)C(=O)CC1C1=CC=CC=C1 ZZIKGBYOHWQFFK-UHFFFAOYSA-N 0.000 description 1
- HRNNWJHAGDNBQH-UHFFFAOYSA-N tert-butyl 6-phenyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine-5-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC=2C=NNC=2CC1C1=CC=CC=C1 HRNNWJHAGDNBQH-UHFFFAOYSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000030968 tissue homeostasis Effects 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229940042129 topical gel Drugs 0.000 description 1
- 229940100615 topical ointment Drugs 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 229940041677 topical spray Drugs 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- 108091005703 transmembrane proteins Proteins 0.000 description 1
- 102000035160 transmembrane proteins Human genes 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61P25/28—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74136605P | 2005-12-01 | 2005-12-01 | |
| US60/741,366 | 2005-12-01 | ||
| PCT/US2006/046039 WO2007064914A2 (en) | 2005-12-01 | 2006-12-01 | 5-(arylsulfonyl)-pyrazolopiperidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2632227A1 true CA2632227A1 (en) | 2007-06-07 |
Family
ID=38092841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002632227A Abandoned CA2632227A1 (en) | 2005-12-01 | 2006-12-01 | 5-(arylsulfonyl)-pyrazolopiperidines |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US7732609B2 (https=) |
| EP (1) | EP1957458A2 (https=) |
| JP (1) | JP2009518301A (https=) |
| KR (1) | KR20080073359A (https=) |
| CN (1) | CN101370776A (https=) |
| AR (1) | AR057959A1 (https=) |
| AU (1) | AU2006320423B2 (https=) |
| BR (1) | BRPI0619633A2 (https=) |
| CA (1) | CA2632227A1 (https=) |
| EA (1) | EA014906B1 (https=) |
| EC (1) | ECSP088593A (https=) |
| IL (1) | IL190608A0 (https=) |
| MA (1) | MA30089B1 (https=) |
| MY (1) | MY149422A (https=) |
| NZ (1) | NZ568109A (https=) |
| PE (1) | PE20071090A1 (https=) |
| TW (1) | TW200736255A (https=) |
| WO (1) | WO2007064914A2 (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2029602E (pt) * | 2006-05-31 | 2010-07-08 | Galapagos Nv | Compostos de triazolopirazina uteis para o tratamento de doenãas degenerativas e inflamatërias |
| JP2010528036A (ja) * | 2007-05-25 | 2010-08-19 | エラン ファーマシューティカルズ，インコーポレイテッド | γセクレターゼの阻害剤としてのピラゾロピロリジン |
| MX2010010773A (es) | 2008-04-01 | 2011-04-11 | Abbott Gmbh & Co Kg | Tetrahidroisoquinolinas, composiciones farmaceuticas que las contienen y su uso en terapia. |
| TW201038569A (en) * | 2009-02-16 | 2010-11-01 | Abbott Gmbh & Co Kg | Heterocyclic compounds, pharmaceutical compositions containing them, and their use in therapy |
| AR075442A1 (es) | 2009-02-16 | 2011-03-30 | Abbott Gmbh & Co Kg | Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia |
| JP2012521993A (ja) * | 2009-03-25 | 2012-09-20 | エラン ファーマシューティカルズ，インコーポレイテッド | 縮合三環式スルホンアミドの製造プロセス |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9045459B2 (en) | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8877794B2 (en) | 2010-08-13 | 2014-11-04 | Abbott Laboratories | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9309200B2 (en) | 2011-05-12 | 2016-04-12 | AbbVie Deutschland GmbH & Co. KG | Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| CA2844275A1 (en) | 2011-08-05 | 2013-02-14 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| MX2014006004A (es) | 2011-11-18 | 2015-04-16 | Abbvie Deutschland | Derivados de aminobenzociclohepteno, aminotetralina, aminoindano y fenalcilamina n-sustituidas, composiciones farmaceuticas que los contienen, y su uso en terapia. |
| US9365512B2 (en) | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9656955B2 (en) | 2013-03-15 | 2017-05-23 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9650334B2 (en) | 2013-03-15 | 2017-05-16 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| CA2924689A1 (en) | 2013-10-17 | 2015-04-23 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| MX2016004934A (es) | 2013-10-17 | 2016-12-20 | Abbvie Deutschland | Derivados de aminotetralina y aminoindano, composiciones farmaceuticas que los contienen, y su uso en terapia. |
| CN104059063A (zh) * | 2014-04-03 | 2014-09-24 | 丽水绿氟科技有限公司 | 7,7-二氟-4,5,6,7-四氢吡唑并[4,3-c]吡啶及其衍生物的制备方法 |
| BR112020018094A2 (pt) | 2018-03-08 | 2020-12-22 | Incyte Corporation | Compostos de aminopirazina diol como inibidores de pi3k-¿ |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL319758A1 (en) * | 1994-10-20 | 1997-08-18 | Pfizer | Bicyclic tetrahydropyrasole pyridines and their application as medicines |
| ES2349762T3 (es) * | 2000-08-10 | 2011-01-11 | Pfizer Italia S.R.L. | Biciclo-pirazoles activos como inhibidores de quinasas, procedimientos para su preparación y composiciones farmacéuticas que los comprenden. |
| US7375115B2 (en) * | 2001-10-09 | 2008-05-20 | Kyorin Pharmaceutical Co., Ltd. | 4-(2-furoyl) aminopiperidines, intermediates in synthesizing the same, process for producing the same and medicinal use of the same |
| AU2003292724A1 (en) * | 2002-12-27 | 2004-07-29 | Japan Tobacco Inc. | Fused n-containing heterocyclic compounds and medicinal use thereof |
| CA2567343A1 (en) * | 2004-05-20 | 2005-12-01 | Elan Pharmaceuticals, Inc. | N-cyclic sulfonamido inhibitors of gamma secretase |
| US20060089378A1 (en) * | 2004-10-27 | 2006-04-27 | Mingde Xia | Tetrahydro-pyridinyl pyrazole cannabinoid modulators |
| DE102005002500A1 (de) * | 2005-01-19 | 2006-07-27 | Sanofi-Aventis Deutschland Gmbh | Tetrahydrofuranderivate als Inhibitoren von Matrix-Metalloproteinasen |
| TW200716628A (en) * | 2005-03-22 | 2007-05-01 | Astrazeneca Ab | Novel compounds |
| DE102005016170A1 (de) * | 2005-04-07 | 2006-10-12 | Grünenthal GmbH | 4,5,6,7- Tetrahydro-isoxazolo(4,5c)pyridin-Verbindungen und deren Verwendung zur Herstellung von Arzneimitteln |
| BRPI0614944A2 (pt) | 2005-08-19 | 2011-04-26 | Elan Pharm Inc | inibidores sulfonamido n-bicìclicos ponte de gama-secretase |
-
2006
- 2006-12-01 AR ARP060105326A patent/AR057959A1/es not_active Application Discontinuation
- 2006-12-01 AU AU2006320423A patent/AU2006320423B2/en not_active Ceased
- 2006-12-01 EP EP06844721A patent/EP1957458A2/en not_active Withdrawn
- 2006-12-01 BR BRPI0619633-0A patent/BRPI0619633A2/pt not_active Application Discontinuation
- 2006-12-01 US US11/566,070 patent/US7732609B2/en not_active Expired - Fee Related
- 2006-12-01 CN CNA2006800451866A patent/CN101370776A/zh active Pending
- 2006-12-01 MY MYPI20081060A patent/MY149422A/en unknown
- 2006-12-01 EA EA200801481A patent/EA014906B1/ru not_active IP Right Cessation
- 2006-12-01 PE PE2006001542A patent/PE20071090A1/es not_active Application Discontinuation
- 2006-12-01 TW TW095144766A patent/TW200736255A/zh unknown
- 2006-12-01 NZ NZ568109A patent/NZ568109A/en not_active IP Right Cessation
- 2006-12-01 CA CA002632227A patent/CA2632227A1/en not_active Abandoned
- 2006-12-01 WO PCT/US2006/046039 patent/WO2007064914A2/en not_active Ceased
- 2006-12-01 JP JP2008543496A patent/JP2009518301A/ja active Pending
- 2006-12-01 KR KR1020087015935A patent/KR20080073359A/ko not_active Ceased
-
2008
- 2008-04-03 IL IL190608A patent/IL190608A0/en unknown
- 2008-06-26 MA MA31080A patent/MA30089B1/fr unknown
- 2008-07-01 EC EC2008008593A patent/ECSP088593A/es unknown
-
2010
- 2010-06-08 US US12/796,441 patent/US20100267747A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EA014906B1 (ru) | 2011-02-28 |
| JP2009518301A (ja) | 2009-05-07 |
| AU2006320423A1 (en) | 2007-06-07 |
| WO2007064914A2 (en) | 2007-06-07 |
| ECSP088593A (es) | 2008-08-29 |
| EA200801481A1 (ru) | 2009-02-27 |
| US7732609B2 (en) | 2010-06-08 |
| AR057959A1 (es) | 2007-12-26 |
| US20070155753A1 (en) | 2007-07-05 |
| EP1957458A2 (en) | 2008-08-20 |
| AU2006320423B2 (en) | 2012-06-21 |
| TW200736255A (en) | 2007-10-01 |
| WO2007064914A8 (en) | 2008-05-15 |
| BRPI0619633A2 (pt) | 2011-10-04 |
| PE20071090A1 (es) | 2007-10-24 |
| MY149422A (en) | 2013-08-30 |
| CN101370776A (zh) | 2009-02-18 |
| NZ568109A (en) | 2011-07-29 |
| WO2007064914A3 (en) | 2007-12-27 |
| KR20080073359A (ko) | 2008-08-08 |
| IL190608A0 (en) | 2008-11-03 |
| MA30089B1 (fr) | 2008-12-01 |
| US20100267747A1 (en) | 2010-10-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20131203 |