JP2006512366A5 - - Google Patents
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- JP2006512366A5 JP2006512366A5 JP2004562221A JP2004562221A JP2006512366A5 JP 2006512366 A5 JP2006512366 A5 JP 2006512366A5 JP 2004562221 A JP2004562221 A JP 2004562221A JP 2004562221 A JP2004562221 A JP 2004562221A JP 2006512366 A5 JP2006512366 A5 JP 2006512366A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- het
- methyl
- optionally substituted
- pyrazolo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 182
- 229910052760 oxygen Inorganic materials 0.000 claims 56
- 229910052717 sulfur Inorganic materials 0.000 claims 53
- 125000004093 cyano group Chemical group *C#N 0.000 claims 49
- -1 hydroxy, amino Chemical group 0.000 claims 48
- 125000000623 heterocyclic group Chemical group 0.000 claims 47
- 229910052736 halogen Inorganic materials 0.000 claims 40
- 150000002367 halogens Chemical class 0.000 claims 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 40
- 125000005842 heteroatom Chemical group 0.000 claims 30
- 229920006395 saturated elastomer Polymers 0.000 claims 30
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 28
- 229910052757 nitrogen Inorganic materials 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 24
- 125000001424 substituent group Chemical group 0.000 claims 24
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 20
- 125000004122 cyclic group Chemical group 0.000 claims 19
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 18
- 229910052799 carbon Inorganic materials 0.000 claims 16
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 12
- 125000001188 haloalkyl group Chemical group 0.000 claims 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 11
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 11
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims 11
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 11
- 125000003107 substituted aryl group Chemical group 0.000 claims 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 8
- UXWAJSLYHVAVKJ-UHFFFAOYSA-N 2-hydrazinyl-2-oxoacetic acid Chemical compound NNC(=O)C(O)=O UXWAJSLYHVAVKJ-UHFFFAOYSA-N 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 8
- 125000002619 bicyclic group Chemical group 0.000 claims 8
- 125000002950 monocyclic group Chemical group 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000004423 acyloxy group Chemical group 0.000 claims 7
- 125000005236 alkanoylamino group Chemical group 0.000 claims 7
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 241000590002 Helicobacter pylori Species 0.000 claims 5
- 229940037467 helicobacter pylori Drugs 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000004486 1-methylpiperidin-3-yl group Chemical group CN1CC(CCC1)* 0.000 claims 4
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 208000015181 infectious disease Diseases 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 4
- 125000006413 ring segment Chemical group 0.000 claims 4
- 238000011282 treatment Methods 0.000 claims 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- OLLUIQZCXQBQSK-UHFFFAOYSA-N n-[2-[(6-chloroquinolin-4-yl)methyl]-3-(4-cyano-1-methylpyrrol-2-yl)-5-methyl-4-oxopyrazolo[3,4-d]pyrimidin-6-yl]-3-methylbutanamide Chemical compound C=12C(=O)N(C)C(NC(=O)CC(C)C)=NC2=NN(CC=2C3=CC(Cl)=CC=C3N=CC=2)C=1C1=CC(C#N)=CN1C OLLUIQZCXQBQSK-UHFFFAOYSA-N 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- WMHFDKFVTVNHQC-UHFFFAOYSA-N 1-[2-[(6-chloroquinolin-4-yl)methyl]-3-(4-cyano-1-methylpyrrol-2-yl)-5-methyl-4-oxopyrazolo[3,4-d]pyrimidin-6-yl]-3-ethylurea Chemical compound C=12C(=O)N(C)C(NC(=O)NCC)=NC2=NN(CC=2C3=CC(Cl)=CC=C3N=CC=2)C=1C1=CC(C#N)=CN1C WMHFDKFVTVNHQC-UHFFFAOYSA-N 0.000 claims 1
- FOSBPPDZQFIBKJ-UHFFFAOYSA-N 2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-5-methyl-3-(3-methylimidazol-4-yl)-4-sulfanylidenepyrazolo[3,4-d]pyrimidin-6-one Chemical compound CN1C=NC=C1C1=C2C(=S)N(C)C(=O)N(CC3CC3)C2=NN1CC1=CC=NC2=CC=C(Cl)C=C12 FOSBPPDZQFIBKJ-UHFFFAOYSA-N 0.000 claims 1
- GYDJJDMTXJIGHU-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-7-(2-methylpropyl)-2-(naphthalen-1-ylmethyl)-3-pyridin-4-ylpyrazolo[3,4-d]pyrimidin-6-one Chemical compound C=12C(N3CCN(C)CC3)=NC(=O)N(CC(C)C)C2=NN(CC=2C3=CC=CC=C3C=CC=2)C=1C1=CC=NC=C1 GYDJJDMTXJIGHU-UHFFFAOYSA-N 0.000 claims 1
- CNCXFTXRDGKTDR-UHFFFAOYSA-N 4-(dimethylamino)-7-(2-methylpropyl)-2-(naphthalen-1-ylmethyl)-3-pyridin-4-ylpyrazolo[3,4-d]pyrimidin-6-one Chemical compound C=12C(N(C)C)=NC(=O)N(CC(C)C)C2=NN(CC=2C3=CC=CC=C3C=CC=2)C=1C1=CC=NC=C1 CNCXFTXRDGKTDR-UHFFFAOYSA-N 0.000 claims 1
- HQNUONYUXJRRGO-UHFFFAOYSA-N 4-(methylamino)-1,2-dihydropyrazolo[3,4-d]pyrimidin-6-one Chemical compound CNC1=NC(=O)N=C2NNC=C12 HQNUONYUXJRRGO-UHFFFAOYSA-N 0.000 claims 1
- HKDAAJOOEJJXGO-UHFFFAOYSA-N 4-(methylamino)-7-(2-methylpropyl)-2-(naphthalen-1-ylmethyl)-3-pyridin-4-ylpyrazolo[3,4-d]pyrimidin-6-one Chemical compound C=12C(NC)=NC(=O)N(CC(C)C)C2=NN(CC=2C3=CC=CC=C3C=CC=2)C=1C1=CC=NC=C1 HKDAAJOOEJJXGO-UHFFFAOYSA-N 0.000 claims 1
- ZBYRJOXGXSUWSZ-UHFFFAOYSA-N 4-amino-2-[(6-chloroquinolin-4-yl)methyl]-7-(2-methylpropyl)-3-(1-methylpyrrol-2-yl)pyrazolo[3,4-d]pyrimidin-6-one Chemical compound C=12C(N)=NC(=O)N(CC(C)C)C2=NN(CC=2C3=CC(Cl)=CC=C3N=CC=2)C=1C1=CC=CN1C ZBYRJOXGXSUWSZ-UHFFFAOYSA-N 0.000 claims 1
- RIQCRMGKJGSOKL-UHFFFAOYSA-N 4-amino-7-(2-methylpropyl)-2-(naphthalen-1-ylmethyl)-3-pyridin-4-ylpyrazolo[3,4-d]pyrimidin-6-one Chemical compound C=12C(N)=NC(=O)N(CC(C)C)C2=NN(CC=2C3=CC=CC=C3C=CC=2)C=1C1=CC=NC=C1 RIQCRMGKJGSOKL-UHFFFAOYSA-N 0.000 claims 1
- QMLYVUZBIAAJEP-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-4-(2,2-dimethylhydrazinyl)-7-(2-methylpropyl)-6-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound C=12C(NN(C)C)=NC(=O)N(CC(C)C)C2=NN(CC=2C3=CC(Cl)=CC=C3N=CC=2)C=1C1=CC(C#N)=CN1C QMLYVUZBIAAJEP-UHFFFAOYSA-N 0.000 claims 1
- DDUJQRINUUSATH-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-4-(2-hydroxyethylamino)-7-(2-methylpropyl)-6-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound C=12C(NCCO)=NC(=O)N(CC(C)C)C2=NN(CC=2C3=CC(Cl)=CC=C3N=CC=2)C=1C1=CC(C#N)=CN1C DDUJQRINUUSATH-UHFFFAOYSA-N 0.000 claims 1
- KQYJNBWOWUEIDW-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-4-(cyclopropylamino)-7-(2-methylpropyl)-6-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound C=12C(NC3CC3)=NC(=O)N(CC(C)C)C2=NN(CC=2C3=CC(Cl)=CC=C3N=CC=2)C=1C1=CC(C#N)=CN1C KQYJNBWOWUEIDW-UHFFFAOYSA-N 0.000 claims 1
- RCMLFJBVAMYCKS-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-4-(dimethylamino)-7-(2-methylpropyl)-6-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound C=12C(N(C)C)=NC(=O)N(CC(C)C)C2=NN(CC=2C3=CC(Cl)=CC=C3N=CC=2)C=1C1=CC(C#N)=CN1C RCMLFJBVAMYCKS-UHFFFAOYSA-N 0.000 claims 1
- OONJOMXXMJPXMB-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-4-(hydroxyamino)-7-(2-methylpropyl)-6-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound C=12C(NO)=NC(=O)N(CC(C)C)C2=NN(CC=2C3=CC(Cl)=CC=C3N=CC=2)C=1C1=CC(C#N)=CN1C OONJOMXXMJPXMB-UHFFFAOYSA-N 0.000 claims 1
- HPRPWZCZFAHUEA-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-4-(methylamino)-7-(2-methylpropyl)-6-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound C=12C(NC)=NC(=O)N(CC(C)C)C2=NN(CC=2C3=CC(Cl)=CC=C3N=CC=2)C=1C1=CC(C#N)=CN1C HPRPWZCZFAHUEA-UHFFFAOYSA-N 0.000 claims 1
- XUIUADSSDASZOS-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-4-hydrazinyl-7-(2-methylpropyl)-6-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound C=12C(NN)=NC(=O)N(CC(C)C)C2=NN(CC=2C3=CC(Cl)=CC=C3N=CC=2)C=1C1=CC(C#N)=CN1C XUIUADSSDASZOS-UHFFFAOYSA-N 0.000 claims 1
- GHDFCCXMBSVWFI-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-6-(cyclopropylmethylamino)-4-(methylamino)pyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound N=1C2=NN(CC=3C4=CC(Cl)=CC=C4N=CC=3)C(C=3N(C=C(C=3)C#N)C)=C2C(NC)=NC=1NCC1CC1 GHDFCCXMBSVWFI-UHFFFAOYSA-N 0.000 claims 1
- LMYKGRJFOBBZBB-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-6-(cyclopropylmethylamino)-5-methyl-4-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound CN1C=C(C#N)C=C1C1=C2C(=O)N(C)C(NCC3CC3)=NC2=NN1CC1=CC=NC2=CC=C(Cl)C=C12 LMYKGRJFOBBZBB-UHFFFAOYSA-N 0.000 claims 1
- MAVXHEFSRYLRFP-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-6-[cyclopropylmethyl(methyl)amino]-5-methyl-4-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound N=1C2=NN(CC=3C4=CC(Cl)=CC=C4N=CC=3)C(C=3N(C=C(C=3)C#N)C)=C2C(=O)N(C)C=1N(C)CC1CC1 MAVXHEFSRYLRFP-UHFFFAOYSA-N 0.000 claims 1
- UOITUYIRMJPNFW-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-7-(2-methylpropyl)-6-oxo-4-(propylamino)pyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound C=12C(NCCC)=NC(=O)N(CC(C)C)C2=NN(CC=2C3=CC(Cl)=CC=C3N=CC=2)C=1C1=CC(C#N)=CN1C UOITUYIRMJPNFW-UHFFFAOYSA-N 0.000 claims 1
- YVUPPRFJSQNAJX-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-4-(2-hydroxybutylamino)-6-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound C12=NN(CC=3C4=CC(Cl)=CC=C4N=CC=3)C(C=3N(C=C(C=3)C#N)C)=C2C(NCC(O)CC)=NC(=O)N1CC1CC1 YVUPPRFJSQNAJX-UHFFFAOYSA-N 0.000 claims 1
- XSMDUBLHXOUMGT-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-4-(methylamino)-6-methyliminopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound C12=NN(CC=3C4=CC(Cl)=CC=C4N=CC=3)C(C=3N(C=C(C=3)C#N)C)=C2C(NC)=N\C(=N\C)N1CC1CC1 XSMDUBLHXOUMGT-UHFFFAOYSA-N 0.000 claims 1
- UZALJGJBYXBJQM-MRXNPFEDSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-4-[[(2r)-2-hydroxypropyl]amino]-6-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound C12=NN(CC=3C4=CC(Cl)=CC=C4N=CC=3)C(C=3N(C=C(C=3)C#N)C)=C2C(NC[C@H](O)C)=NC(=O)N1CC1CC1 UZALJGJBYXBJQM-MRXNPFEDSA-N 0.000 claims 1
- XGIZVGCQMGYMPF-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-4-imino-5-methyl-6-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound CN1C=C(C#N)C=C1C1=C2C(=N)N(C)C(=O)N(CC3CC3)C2=NN1CC1=CC=NC2=CC=C(Cl)C=C12 XGIZVGCQMGYMPF-UHFFFAOYSA-N 0.000 claims 1
- HUTVYDIPILCFEP-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-4-methoxy-6-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound C12=NN(CC=3C4=CC(Cl)=CC=C4N=CC=3)C(C=3N(C=C(C=3)C#N)C)=C2C(OC)=NC(=O)N1CC1CC1 HUTVYDIPILCFEP-UHFFFAOYSA-N 0.000 claims 1
- RYPUXSXXVALVJC-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-4-methylsulfanyl-6-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound C12=NN(CC=3C4=CC(Cl)=CC=C4N=CC=3)C(C=3N(C=C(C=3)C#N)C)=C2C(SC)=NC(=O)N1CC1CC1 RYPUXSXXVALVJC-UHFFFAOYSA-N 0.000 claims 1
- DHSMICAQRHZYBK-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-5-methyl-4-oxo-6-sulfanylidenepyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound CN1C=C(C#N)C=C1C1=C2C(=O)N(C)C(=S)N(CC3CC3)C2=NN1CC1=CC=NC2=CC=C(Cl)C=C12 DHSMICAQRHZYBK-UHFFFAOYSA-N 0.000 claims 1
- NNRQVFYFIZONSL-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-5-methyl-6-oxo-4h-pyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound C1CC1CN1C(=O)N(C)CC=2C1=NN(CC=1C3=CC(Cl)=CC=C3N=CC=1)C=2C1=CC(C#N)=CN1C NNRQVFYFIZONSL-UHFFFAOYSA-N 0.000 claims 1
- XNTNMXMOVZGZBX-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-6-imino-5-methyl-4-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound CN1C=C(C#N)C=C1C1=C2C(=O)N(C)C(=N)N(CC3CC3)C2=NN1CC1=CC=NC2=CC=C(Cl)C=C12 XNTNMXMOVZGZBX-UHFFFAOYSA-N 0.000 claims 1
- GZQUXGIBGNJIEG-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-6-oxo-4,5-dihydropyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound CN1C=C(C#N)C=C1C1=C(CNC(=O)N2CC3CC3)C2=NN1CC1=CC=NC2=CC=C(Cl)C=C12 GZQUXGIBGNJIEG-UHFFFAOYSA-N 0.000 claims 1
- MUCRNTHMLXWZDJ-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-6-oxo-4-pyrrol-1-ylpyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound CN1C=C(C#N)C=C1C1=C2C(N3C=CC=C3)=NC(=O)N(CC3CC3)C2=NN1CC1=CC=NC2=CC=C(Cl)C=C12 MUCRNTHMLXWZDJ-UHFFFAOYSA-N 0.000 claims 1
- CDCXXPTXUBWPHS-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-6-oxo-4-sulfanylidenepyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound CN1C=C(C#N)C=C1C1=C2C(=S)NC(=O)N(CC3CC3)C2=NN1CC1=CC=NC2=CC=C(Cl)C=C12 CDCXXPTXUBWPHS-UHFFFAOYSA-N 0.000 claims 1
- GXSSXOZLPJPIFB-UHFFFAOYSA-N 5-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-6-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound CN1C=C(C#N)C=C1C1=C2C=NC(=O)N(CC3CC3)C2=NN1CC1=CC=NC2=CC=C(Cl)C=C12 GXSSXOZLPJPIFB-UHFFFAOYSA-N 0.000 claims 1
- YEHALFCBJLQGOY-UHFFFAOYSA-N 5-[4-amino-2-[(6-chloroquinolin-4-yl)methyl]-7-(2-methylpropyl)-6-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound C=12C(N)=NC(=O)N(CC(C)C)C2=NN(CC=2C3=CC(Cl)=CC=C3N=CC=2)C=1C1=CC(C#N)=CN1C YEHALFCBJLQGOY-UHFFFAOYSA-N 0.000 claims 1
- VKIQPLVVCDWMHD-UHFFFAOYSA-N 5-[6-amino-2-[(6-chloroquinolin-4-yl)methyl]-5-methyl-4-oxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylpyrrole-3-carbonitrile Chemical compound CN1C=C(C#N)C=C1C1=C2C(=O)N(C)C(N)=NC2=NN1CC1=CC=NC2=CC=C(Cl)C=C12 VKIQPLVVCDWMHD-UHFFFAOYSA-N 0.000 claims 1
- MLLHFHURWWJCAE-KDJFERLWSA-N C=1C=NC2=CC=C(Cl)C=C2C=1CN1N=C2N(CC3CC3)C(=N/C)/N(C)C(=O)C2=C1C1=CC(C#N)=CN1C Chemical compound C=1C=NC2=CC=C(Cl)C=C2C=1CN1N=C2N(CC3CC3)C(=N/C)/N(C)C(=O)C2=C1C1=CC(C#N)=CN1C MLLHFHURWWJCAE-KDJFERLWSA-N 0.000 claims 1
- 206010019375 Helicobacter infections Diseases 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- JCEMODISQYSBEB-BXVZCJGGSA-N N=1C2=NN(CC=3C4=CC(Cl)=CC=C4N=CC=3)C(C=3N(C=C(C=3)C#N)C)=C2C(=N/C)/N(C)C=1NCC1CC1 Chemical compound N=1C2=NN(CC=3C4=CC(Cl)=CC=C4N=CC=3)C(C=3N(C=C(C=3)C#N)C)=C2C(=N/C)/N(C)C=1NCC1CC1 JCEMODISQYSBEB-BXVZCJGGSA-N 0.000 claims 1
- HEUUPWDHDBGQPN-JVCXMKTPSA-N c12c(=N/C)/n(C)c(=O)n(CC3CC3)c2nn(Cc2ccnc3ccc(Cl)cc32)c1-c1n(C)cc(C#N)c1 Chemical compound c12c(=N/C)/n(C)c(=O)n(CC3CC3)c2nn(Cc2ccnc3ccc(Cl)cc32)c1-c1n(C)cc(C#N)c1 HEUUPWDHDBGQPN-JVCXMKTPSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- WYNIUVFTTPVXHN-UHFFFAOYSA-N ethyl n-[2-[(6-chloroquinolin-4-yl)methyl]-3-(4-cyano-1-methylpyrrol-2-yl)-5-methyl-4-oxopyrazolo[3,4-d]pyrimidin-6-yl]carbamate Chemical compound C=12C(=O)N(C)C(NC(=O)OCC)=NC2=NN(CC=2C3=CC(Cl)=CC=C3N=CC=2)C=1C1=CC(C#N)=CN1C WYNIUVFTTPVXHN-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- SAYQYUMGGZFXHF-UHFFFAOYSA-N n'-[2-[(6-chloroquinolin-4-yl)methyl]-3-(4-cyano-1-methylpyrrol-2-yl)-5-methyl-4-oxopyrazolo[3,4-d]pyrimidin-6-yl]-n,n-dimethylmethanimidamide Chemical compound C=12C(=O)N(C)C(N=CN(C)C)=NC2=NN(CC=2C3=CC(Cl)=CC=C3N=CC=2)C=1C1=CC(C#N)=CN1C SAYQYUMGGZFXHF-UHFFFAOYSA-N 0.000 claims 1
- CKOXCYCDFQGAFS-UHFFFAOYSA-N n-[2-[(6-chloroquinolin-4-yl)methyl]-3-(4-cyano-1-methylpyrrol-2-yl)-5-methyl-4-oxopyrazolo[3,4-d]pyrimidin-6-yl]propane-1-sulfonamide Chemical compound C=12C(=O)N(C)C(NS(=O)(=O)CCC)=NC2=NN(CC=2C3=CC(Cl)=CC=C3N=CC=2)C=1C1=CC(C#N)=CN1C CKOXCYCDFQGAFS-UHFFFAOYSA-N 0.000 claims 1
- BOOAUMLQBYWQTH-UHFFFAOYSA-N n-[2-[(6-chloroquinolin-4-yl)methyl]-3-(4-cyano-1-methylpyrrol-2-yl)-7-(2-methylpropyl)-6-oxopyrazolo[3,4-d]pyrimidin-4-yl]acetamide Chemical compound C=12C(NC(C)=O)=NC(=O)N(CC(C)C)C2=NN(CC=2C3=CC(Cl)=CC=C3N=CC=2)C=1C1=CC(C#N)=CN1C BOOAUMLQBYWQTH-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
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| PCT/SE2003/002033 WO2004056831A1 (en) | 2002-12-20 | 2003-12-19 | PYRAZOLO [3,4-d] PYRIMIDINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF H.PYLORI INFECTION |
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| JP2006512366A JP2006512366A (ja) | 2006-04-13 |
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| IL160307A0 (en) | 2001-08-31 | 2004-07-25 | Univ Rockefeller | Phosphodiesterase activity and regulation of phosphodiesterase 1-b-mediated signaling in brain |
| US9255099B2 (en) | 2006-06-06 | 2016-02-09 | Intra-Cellular Therapies, Inc. | Pyrazolo[3,4-D]pyrimidine-4,6(5H,7H)-diones as phosphodiesterase 1 inhibitors |
| JP2010509399A (ja) | 2006-11-13 | 2010-03-25 | イントラ−セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| AU2008331833A1 (en) | 2007-12-06 | 2009-06-11 | Intra-Cellular Therapies, Inc | Organic compounds |
| JP5216912B2 (ja) | 2008-04-29 | 2013-06-19 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｃｒ１受容体拮抗薬としてのインダゾール化合物 |
| JP5411927B2 (ja) * | 2008-05-06 | 2014-02-12 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｃｒ１アンタゴニストとしてのピラゾール化合物 |
| KR20110060904A (ko) | 2008-09-26 | 2011-06-08 | 베링거 인겔하임 인터내셔날 게엠베하 | Ｃｃｒ1 수용체 길항제로서의 아자인다졸 화합물 |
| SG171777A1 (en) | 2008-12-06 | 2011-07-28 | Intra Cellular Therapies Inc | Organic compounds |
| GEP20146029B (en) | 2008-12-06 | 2014-02-10 | Intracellular Therapies Inc | Organic compounds |
| US8927556B2 (en) | 2008-12-06 | 2015-01-06 | Intra-Cellular Therapies, Inc. | 1H-pyrrolo[3,4-D]pyrimidin-2(6H)-one compounds |
| SG10201507362TA (en) | 2009-08-05 | 2015-10-29 | Intra Cellular Therapies Inc | Novel Regulatory Proteins And Inhibitors |
| RS53130B (sr) | 2009-10-21 | 2014-06-30 | Boehringer Ingelheim International Gmbh | Jedinjenja indazola i pirazolopiridina kao ccr1 receptor antagonisti |
| JP5542214B2 (ja) | 2009-10-27 | 2014-07-09 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｃｒ１受容体アンタゴニストとしての複素環化合物 |
| MX2012006524A (es) * | 2009-12-08 | 2012-07-17 | Boehringer Ingelheim Int | Proceso para la sintesis de compuestos intermedios de utilidad para preparar compuestos sustituidos de indazol y azaindol. |
| WO2011137109A1 (en) | 2010-04-30 | 2011-11-03 | Boehringer Ingelheim International Gmbh | Azaindazole amide compounds as ccr1 receptor antagonists |
| EP2590657A4 (en) | 2010-05-31 | 2014-02-12 | Intra Cellular Therapies Inc | ORGANIC CONNECTIONS |
| US9434730B2 (en) | 2010-05-31 | 2016-09-06 | Intra-Cellular Therapies, Inc. | PDE1 inhibitor compounds |
| US8546442B2 (en) | 2010-12-23 | 2013-10-01 | Boehringer Ingelheim International Gmbh | Pyrazolopiperidine compounds as CCR1 receptor antagonists |
| US9546175B2 (en) | 2014-08-07 | 2017-01-17 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US11786528B2 (en) | 2018-06-04 | 2023-10-17 | Exscientia Ltd. | Pyrazolopyrimidine compounds as adenosine receptor antagonists |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE3839839A1 (de) * | 1988-11-25 | 1990-05-31 | Henning Berlin Gmbh | Mittel zur behandlung von chronisch entzuendlichen darmerkrankungen |
| SE0102315D0 (sv) * | 2001-06-28 | 2001-06-28 | Astrazeneca Ab | Compounds |
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2002
- 2002-12-20 SE SE0203825A patent/SE0203825D0/xx unknown
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2003
- 2003-12-19 WO PCT/SE2003/002033 patent/WO2004056831A1/en not_active Ceased
- 2003-12-19 AU AU2003288869A patent/AU2003288869A1/en not_active Abandoned
- 2003-12-19 AT AT03781250T patent/ATE349448T1/de not_active IP Right Cessation
- 2003-12-19 EP EP03781250A patent/EP1585748B1/en not_active Expired - Lifetime
- 2003-12-19 JP JP2004562221A patent/JP2006512366A/ja active Pending
- 2003-12-19 ES ES03781250T patent/ES2278211T3/es not_active Expired - Lifetime
- 2003-12-19 US US10/539,936 patent/US20070004761A1/en not_active Abandoned
- 2003-12-19 DE DE60310767T patent/DE60310767T2/de not_active Expired - Fee Related
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