AU2006320423B2 - 5-(arylsulfonyl)-pyrazolopiperidines - Google Patents
5-(arylsulfonyl)-pyrazolopiperidines Download PDFInfo
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- AU2006320423B2 AU2006320423B2 AU2006320423A AU2006320423A AU2006320423B2 AU 2006320423 B2 AU2006320423 B2 AU 2006320423B2 AU 2006320423 A AU2006320423 A AU 2006320423A AU 2006320423 A AU2006320423 A AU 2006320423A AU 2006320423 B2 AU2006320423 B2 AU 2006320423B2
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- Australia
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims abstract description 1034
- -1 C1-C 6 alkoxy Chemical group 0.000 claims description 426
- 125000000217 alkyl group Chemical group 0.000 claims description 402
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 333
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 325
- 125000004076 pyridyl group Chemical group 0.000 claims description 304
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 273
- 229910052736 halogen Inorganic materials 0.000 claims description 185
- 150000002367 halogens Chemical class 0.000 claims description 185
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 178
- 125000005843 halogen group Chemical group 0.000 claims description 170
- 125000000335 thiazolyl group Chemical group 0.000 claims description 158
- 125000003545 alkoxy group Chemical group 0.000 claims description 154
- 229910052739 hydrogen Inorganic materials 0.000 claims description 149
- 125000002883 imidazolyl group Chemical group 0.000 claims description 141
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 108
- 239000000203 mixture Substances 0.000 claims description 63
- 125000002971 oxazolyl group Chemical group 0.000 claims description 62
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 60
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 60
- 125000001188 haloalkyl group Chemical group 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 37
- 125000003342 alkenyl group Chemical group 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 150000002431 hydrogen Chemical class 0.000 claims description 32
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 31
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 26
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 25
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 19
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 12
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 12
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 12
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 12
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
- 239000002671 adjuvant Substances 0.000 claims description 9
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- SELYJABLPLKXOY-UHFFFAOYSA-N methyl n,n-dimethylcarbamate Chemical compound COC(=O)N(C)C SELYJABLPLKXOY-UHFFFAOYSA-N 0.000 claims description 7
- WCXFPLXZZSWROM-UHFFFAOYSA-N 1h-pyrazolo[4,3-c]pyridine Chemical compound C1=NC=C2C=NNC2=C1 WCXFPLXZZSWROM-UHFFFAOYSA-N 0.000 claims description 5
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 239000007884 disintegrant Substances 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- IDFPQEHZYBXIFO-GFCCVEGCSA-N (R)-(4-fluoro-2-propylphenyl)-(1H-imidazol-2-yl)methanol Chemical compound CCCc1cc(F)ccc1[C@@H](O)c1ncc[nH]1 IDFPQEHZYBXIFO-GFCCVEGCSA-N 0.000 claims description 2
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 claims description 2
- YNXVSPCMOHSORF-UHFFFAOYSA-N ethyl 5-(4-chlorophenyl)sulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine-4-carboxylate Chemical compound C1CC=2NN=CC=2C(C(=O)OCC)N1S(=O)(=O)C1=CC=C(Cl)C=C1 YNXVSPCMOHSORF-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 125000004169 (C1-C6) alkyl 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
- 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 1
- WDWZCPBEJNKJHZ-UHFFFAOYSA-N 4,6-diethyl-5-(4-fluorophenyl)sulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound CCC1CC2=NNC=C2C(CC)N1S(=O)(=O)C1=CC=C(F)C=C1 WDWZCPBEJNKJHZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- VXZAMCUMOIFIDF-UHFFFAOYSA-N 6-methyl-4-pyrimidin-5-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=CN=CN=C1 VXZAMCUMOIFIDF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- SIZMAOAIVRSPAF-UHFFFAOYSA-N [4-pyrimidin-5-yl-5-[4-(trifluoromethyl)phenyl]sulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-6-yl]methanol Chemical compound OCC1CC=2NN=CC=2C(C=2C=NC=NC=2)N1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 SIZMAOAIVRSPAF-UHFFFAOYSA-N 0.000 claims 1
- XZEDEUHLULQQKX-UHFFFAOYSA-N [5-(4-chlorophenyl)sulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-6-yl]methanol Chemical compound OCC1CC=2NN=CC=2CN1S(=O)(=O)C1=CC=C(Cl)C=C1 XZEDEUHLULQQKX-UHFFFAOYSA-N 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- FRDWVNKKBQHREV-UHFFFAOYSA-N diethyl 5-(4-chlorophenyl)sulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine-4,6-dicarboxylate Chemical compound CCOC(=O)C1CC=2NN=CC=2C(C(=O)OCC)N1S(=O)(=O)C1=CC=C(Cl)C=C1 FRDWVNKKBQHREV-UHFFFAOYSA-N 0.000 claims 1
- FGTCQDBLQPQPQE-UHFFFAOYSA-N ethyl 5-(4-chlorophenyl)sulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine-6-carboxylate Chemical compound CCOC(=O)C1CC=2NN=CC=2CN1S(=O)(=O)C1=CC=C(Cl)C=C1 FGTCQDBLQPQPQE-UHFFFAOYSA-N 0.000 claims 1
- UFJNSBIBVKVMPK-UHFFFAOYSA-N ethyl 5-(4-chlorophenyl)sulfonyl-6-ethyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine-4-carboxylate Chemical compound CCC1CC=2NN=CC=2C(C(=O)OCC)N1S(=O)(=O)C1=CC=C(Cl)C=C1 UFJNSBIBVKVMPK-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 89
- 208000024827 Alzheimer disease Diseases 0.000 abstract description 35
- 208000010877 cognitive disease Diseases 0.000 abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 121
- 125000000753 cycloalkyl group Chemical group 0.000 description 94
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 59
- 125000003373 pyrazinyl group Chemical group 0.000 description 59
- 125000002098 pyridazinyl group Chemical group 0.000 description 57
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 55
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 54
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 48
- 125000003282 alkyl amino group Chemical group 0.000 description 47
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 125000001589 carboacyl group Chemical group 0.000 description 36
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 32
- 125000002632 imidazolidinyl group Chemical group 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 28
- 125000004663 dialkyl amino group Chemical group 0.000 description 26
- 125000001544 thienyl group Chemical group 0.000 description 26
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 description 22
- 125000002757 morpholinyl group Chemical group 0.000 description 22
- 101710137189 Amyloid-beta A4 protein Proteins 0.000 description 21
- 101710151993 Amyloid-beta precursor protein Proteins 0.000 description 21
- 102100022704 Amyloid-beta precursor protein Human genes 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 125000004193 piperazinyl group Chemical group 0.000 description 20
- 239000000460 chlorine Substances 0.000 description 19
- 235000019439 ethyl acetate Nutrition 0.000 description 19
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 19
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- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
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- 125000005994 isobenzotetrahydrofuranyl group Chemical group 0.000 description 1
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- DPDXVBIWZBJGSX-XUTVFYLZSA-N isoboonein Chemical compound C1C(=O)OC[C@@H]2[C@@H](C)[C@@H](O)C[C@@H]21 DPDXVBIWZBJGSX-XUTVFYLZSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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- PREZVEZGASNUKX-UHFFFAOYSA-N methyl 2-[(4-chlorophenyl)sulfonyl-pent-1-yn-3-ylamino]butanoate Chemical compound COC(=O)C(CC)N(C(C#C)CC)S(=O)(=O)C1=CC=C(Cl)C=C1 PREZVEZGASNUKX-UHFFFAOYSA-N 0.000 description 1
- UTVMMYAYJZXJFO-UHFFFAOYSA-N methyl 2-[(4-chlorophenyl)sulfonylamino]butanoate Chemical compound COC(=O)C(CC)NS(=O)(=O)C1=CC=C(Cl)C=C1 UTVMMYAYJZXJFO-UHFFFAOYSA-N 0.000 description 1
- AHAQQEGUPULIOZ-UHFFFAOYSA-N methyl 2-aminobutanoate;hydrochloride Chemical compound Cl.CCC(N)C(=O)OC AHAQQEGUPULIOZ-UHFFFAOYSA-N 0.000 description 1
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
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- 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
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- 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
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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- 235000015424 sodium Nutrition 0.000 description 1
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- 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
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
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- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
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- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
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- 210000002023 somite Anatomy 0.000 description 1
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- 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
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- 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
- 125000005958 tetrahydrothienyl group Chemical group 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
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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
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- 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
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- 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
- 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
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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
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- 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 (2)
| Publication Number | Publication Date |
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| AU2006320423A1 AU2006320423A1 (en) | 2007-06-07 |
| AU2006320423B2 true AU2006320423B2 (en) | 2012-06-21 |
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| Application Number | Title | Priority Date | Filing Date |
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| AU2006320423A Ceased AU2006320423B2 (en) | 2005-12-01 | 2006-12-01 | 5-(arylsulfonyl)-pyrazolopiperidines |
Country Status (18)
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| 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002012242A2 (en) * | 2000-08-10 | 2002-02-14 | Pharmacia Italia S.P.A. | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
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| 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 |
| 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
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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
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2010
- 2010-06-08 US US12/796,441 patent/US20100267747A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002012242A2 (en) * | 2000-08-10 | 2002-02-14 | Pharmacia Italia S.P.A. | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
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 |
| TW200736255A (en) | 2007-10-01 |
| CA2632227A1 (en) | 2007-06-07 |
| 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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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |