JP2008007493A5 - - Google Patents
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- Publication number
- JP2008007493A5 JP2008007493A5 JP2006285609A JP2006285609A JP2008007493A5 JP 2008007493 A5 JP2008007493 A5 JP 2008007493A5 JP 2006285609 A JP2006285609 A JP 2006285609A JP 2006285609 A JP2006285609 A JP 2006285609A JP 2008007493 A5 JP2008007493 A5 JP 2008007493A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- chlorophenyl
- alkyl
- pyrimidine
- unsaturated
- 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.)
- Granted
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 67
- 229920006395 saturated elastomer Polymers 0.000 claims 53
- 125000005843 halogen group Chemical group 0.000 claims 49
- 125000000623 heterocyclic group Chemical group 0.000 claims 35
- 125000003545 alkoxy group Chemical group 0.000 claims 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 29
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims 23
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 20
- -1 pyrazolo [1,5-a] pyrimidine compound Chemical class 0.000 claims 20
- 125000004043 oxo group Chemical group O=* 0.000 claims 17
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 15
- 125000002950 monocyclic group Chemical group 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000003277 amino group Chemical group 0.000 claims 10
- 125000002252 acyl group Chemical group 0.000 claims 9
- 125000002619 bicyclic group Chemical group 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000004434 sulfur atom Chemical group 0.000 claims 6
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical group C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 3
- 230000005494 condensation Effects 0.000 claims 3
- 238000009833 condensation Methods 0.000 claims 3
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000005936 piperidyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims 2
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 2
- 125000002636 imidazolinyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 2
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 2
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 2
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 2
- 125000006085 pyrrolopyridyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims 2
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims 2
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 2
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 1
- VEQUZGUEQFVGEC-UHFFFAOYSA-N 1-[6-(2-chlorophenyl)-7-(4-chlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-3-yl]-2-(1,1-dioxo-1,4-thiazinan-4-yl)ethanone Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)CN3CCS(=O)(=O)CC3)C(C)=NN2C=1C1=CC=C(Cl)C=C1 VEQUZGUEQFVGEC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- QBFGVGOIOVZNRI-UHFFFAOYSA-N 6-(2-bromophenyl)-7-(4-chlorophenyl)-n-cyclopentylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)Br)C=NC2=C(C(=O)NC3CCCC3)C=NN12 QBFGVGOIOVZNRI-UHFFFAOYSA-N 0.000 claims 1
- AKYWKGQCWAEJOF-OAHLLOKOSA-N 6-(2-chlorophenyl)-2-(difluoromethyl)-n-[(3r)-1,1-dioxothiolan-3-yl]-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)N[C@H]3CS(=O)(=O)CC3)C(C(F)F)=NN2C=1C1=CC=C(C(F)(F)F)C=C1 AKYWKGQCWAEJOF-OAHLLOKOSA-N 0.000 claims 1
- AKYWKGQCWAEJOF-HNNXBMFYSA-N 6-(2-chlorophenyl)-2-(difluoromethyl)-n-[(3s)-1,1-dioxothiolan-3-yl]-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)N[C@@H]3CS(=O)(=O)CC3)C(C(F)F)=NN2C=1C1=CC=C(C(F)(F)F)C=C1 AKYWKGQCWAEJOF-HNNXBMFYSA-N 0.000 claims 1
- DVZARUHPTYQMGX-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-2-(difluoromethyl)-n-pyrrolidin-1-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)NN3CCCC3)C(C(F)F)=NN2C=1C1=CC=C(Cl)C=C1 DVZARUHPTYQMGX-UHFFFAOYSA-N 0.000 claims 1
- JZOZVEGKHBURJB-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-2-(methoxymethyl)-n'-methyl-n'-pyridin-2-ylpyrazolo[1,5-a]pyrimidine-3-carbohydrazide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)NN(C)C=3N=CC=CC=3)C(COC)=NN2C=1C1=CC=C(Cl)C=C1 JZOZVEGKHBURJB-UHFFFAOYSA-N 0.000 claims 1
- BIKBIDGOMHVKRR-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-2-(methoxymethyl)-n-pyrrolidin-1-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)NN3CCCC3)C(COC)=NN2C=1C1=CC=C(Cl)C=C1 BIKBIDGOMHVKRR-UHFFFAOYSA-N 0.000 claims 1
- DPOAQDDGINZYMI-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n',n'-dimethylpyrazolo[1,5-a]pyrimidine-3-carbohydrazide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)NN(C)C)C=NN2C=1C1=CC=C(Cl)C=C1 DPOAQDDGINZYMI-UHFFFAOYSA-N 0.000 claims 1
- MKJLQUZGDVYLPO-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n'-(6-ethoxypyridin-3-yl)-n'-methylpyrazolo[1,5-a]pyrimidine-3-carbohydrazide Chemical compound C1=NC(OCC)=CC=C1N(C)NC(=O)C1=C2N=CC(C=3C(=CC=CC=3)Cl)=C(C=3C=CC(Cl)=CC=3)N2N=C1 MKJLQUZGDVYLPO-UHFFFAOYSA-N 0.000 claims 1
- UHNRGAANSILTEJ-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n'-(6-methoxypyridin-3-yl)-n'-methylpyrazolo[1,5-a]pyrimidine-3-carbohydrazide Chemical compound C1=NC(OC)=CC=C1N(C)NC(=O)C1=C2N=CC(C=3C(=CC=CC=3)Cl)=C(C=3C=CC(Cl)=CC=3)N2N=C1 UHNRGAANSILTEJ-UHFFFAOYSA-N 0.000 claims 1
- MDQDPXAOQCFFFE-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n'-methyl-n'-phenylpyrazolo[1,5-a]pyrimidine-3-carbohydrazide Chemical compound C=1C=CC=CC=1N(C)NC(=O)C(=C1N=CC=2C=3C(=CC=CC=3)Cl)C=NN1C=2C1=CC=C(Cl)C=C1 MDQDPXAOQCFFFE-UHFFFAOYSA-N 0.000 claims 1
- BOANGAFVCNVTRF-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n'-methyl-n'-pyridin-2-yl-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carbohydrazide Chemical compound C=1C=CC=NC=1N(C)NC(=O)C(=C1N=CC=2C=3C(=CC=CC=3)Cl)C(C(F)(F)F)=NN1C=2C1=CC=C(Cl)C=C1 BOANGAFVCNVTRF-UHFFFAOYSA-N 0.000 claims 1
- UANLLZWGQLTVJF-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n'-methyl-n'-pyridin-2-ylpyrazolo[1,5-a]pyrimidine-3-carbohydrazide Chemical compound C=1C=CC=NC=1N(C)NC(=O)C(=C1N=CC=2C=3C(=CC=CC=3)Cl)C=NN1C=2C1=CC=C(Cl)C=C1 UANLLZWGQLTVJF-UHFFFAOYSA-N 0.000 claims 1
- IBUUVDQXXWHEFV-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-(1,1-dioxothietan-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)NC3CS(=O)(=O)C3)C=NN12 IBUUVDQXXWHEFV-UHFFFAOYSA-N 0.000 claims 1
- WSVYEKWRVHFEDT-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-(1,1-dioxothiolan-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)NC3CS(=O)(=O)CC3)C=NN12 WSVYEKWRVHFEDT-UHFFFAOYSA-N 0.000 claims 1
- ILLDCALIMWRUBQ-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-(2-methylpropyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)NCC(C)C)C=NN2C=1C1=CC=C(Cl)C=C1 ILLDCALIMWRUBQ-UHFFFAOYSA-N 0.000 claims 1
- LFWDDXPXVNREAW-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-(2-pyridin-2-ylethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)NCCC=3N=CC=CC=3)C=NN12 LFWDDXPXVNREAW-UHFFFAOYSA-N 0.000 claims 1
- QSYOLAFPVZTBPG-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-(oxan-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)NC3CCOCC3)C=NN12 QSYOLAFPVZTBPG-UHFFFAOYSA-N 0.000 claims 1
- KBJPJFZEIUFBAJ-SFHVURJKSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC[C@@H]1CCCN1NC(=O)C1=C2N=CC(C=3C(=CC=CC=3)Cl)=C(C=3C=CC(Cl)=CC=3)N2N=C1 KBJPJFZEIUFBAJ-SFHVURJKSA-N 0.000 claims 1
- MNNDQMYGYUSGRC-QGZVFWFLSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-[(3r)-1,1-dioxothiolan-3-yl]-2-(methoxymethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)N[C@H]3CS(=O)(=O)CC3)C(COC)=NN2C=1C1=CC=C(Cl)C=C1 MNNDQMYGYUSGRC-QGZVFWFLSA-N 0.000 claims 1
- GNVCKJLARKCVDC-OAHLLOKOSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-[(3r)-1,1-dioxothiolan-3-yl]-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)N[C@H]3CS(=O)(=O)CC3)C(C(F)(F)F)=NN2C=1C1=CC=C(Cl)C=C1 GNVCKJLARKCVDC-OAHLLOKOSA-N 0.000 claims 1
- UTAUWLXOIYSMFG-QGZVFWFLSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-[(3r)-1,1-dioxothiolan-3-yl]-2-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)N[C@H]3CS(=O)(=O)CC3)C(C)=NN2C=1C1=CC=C(Cl)C=C1 UTAUWLXOIYSMFG-QGZVFWFLSA-N 0.000 claims 1
- WSVYEKWRVHFEDT-MRXNPFEDSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-[(3r)-1,1-dioxothiolan-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)N[C@H]3CS(=O)(=O)CC3)C=NN12 WSVYEKWRVHFEDT-MRXNPFEDSA-N 0.000 claims 1
- MNNDQMYGYUSGRC-KRWDZBQOSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-[(3s)-1,1-dioxothiolan-3-yl]-2-(methoxymethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)N[C@@H]3CS(=O)(=O)CC3)C(COC)=NN2C=1C1=CC=C(Cl)C=C1 MNNDQMYGYUSGRC-KRWDZBQOSA-N 0.000 claims 1
- UTAUWLXOIYSMFG-KRWDZBQOSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-[(3s)-1,1-dioxothiolan-3-yl]-2-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)N[C@@H]3CS(=O)(=O)CC3)C(C)=NN2C=1C1=CC=C(Cl)C=C1 UTAUWLXOIYSMFG-KRWDZBQOSA-N 0.000 claims 1
- WSVYEKWRVHFEDT-INIZCTEOSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-[(3s)-1,1-dioxothiolan-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)N[C@@H]3CS(=O)(=O)CC3)C=NN12 WSVYEKWRVHFEDT-INIZCTEOSA-N 0.000 claims 1
- ZZBARLOXOSWJIH-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-cyclohexylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)NC3CCCCC3)C=NN12 ZZBARLOXOSWJIH-UHFFFAOYSA-N 0.000 claims 1
- WEWOWORVLKQOIL-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-cyclopentyl-2-methoxypyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)NC3CCCC3)C(OC)=NN2C=1C1=CC=C(Cl)C=C1 WEWOWORVLKQOIL-UHFFFAOYSA-N 0.000 claims 1
- IEZFUCNTEJBXAG-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-cyclopentylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)NC3CCCC3)C=NN12 IEZFUCNTEJBXAG-UHFFFAOYSA-N 0.000 claims 1
- GQUVOYCXSVPVCT-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-cyclopropylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)NC3CC3)C=NN12 GQUVOYCXSVPVCT-UHFFFAOYSA-N 0.000 claims 1
- AATPLCDAPJRFJC-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-ethylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)NCC)C=NN2C=1C1=CC=C(Cl)C=C1 AATPLCDAPJRFJC-UHFFFAOYSA-N 0.000 claims 1
- ZVJOCFYQVAFMLR-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-piperidin-1-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)NN3CCCCC3)C=NN12 ZVJOCFYQVAFMLR-UHFFFAOYSA-N 0.000 claims 1
- JIMWKAUTZYQIIL-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-chlorophenyl)-n-pyrrolidin-1-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)NN3CCCC3)C=NN12 JIMWKAUTZYQIIL-UHFFFAOYSA-N 0.000 claims 1
- WAJQWLSACZDJCN-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-(4-cyanophenyl)-n-cyclopentylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound ClC1=CC=CC=C1C1=C(C=2C=CC(=CC=2)C#N)N2N=CC(C(=O)NC3CCCC3)=C2N=C1 WAJQWLSACZDJCN-UHFFFAOYSA-N 0.000 claims 1
- OUFAAUTXKQBTNJ-MRXNPFEDSA-N 6-(2-chlorophenyl)-7-[4-(difluoromethyl)phenyl]-n-[(3r)-1,1-dioxothiolan-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(C(F)F)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)N[C@H]3CS(=O)(=O)CC3)C=NN12 OUFAAUTXKQBTNJ-MRXNPFEDSA-N 0.000 claims 1
- OUFAAUTXKQBTNJ-INIZCTEOSA-N 6-(2-chlorophenyl)-7-[4-(difluoromethyl)phenyl]-n-[(3s)-1,1-dioxothiolan-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(C(F)F)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)N[C@@H]3CS(=O)(=O)CC3)C=NN12 OUFAAUTXKQBTNJ-INIZCTEOSA-N 0.000 claims 1
- VZJOGKVKWHCJNG-UHFFFAOYSA-N 6-(2-chlorophenyl)-n'-(3-chlorophenyl)-7-(4-chlorophenyl)-n'-methylpyrazolo[1,5-a]pyrimidine-3-carbohydrazide Chemical compound C=1C=CC(Cl)=CC=1N(C)NC(=O)C(=C1N=CC=2C=3C(=CC=CC=3)Cl)C=NN1C=2C1=CC=C(Cl)C=C1 VZJOGKVKWHCJNG-UHFFFAOYSA-N 0.000 claims 1
- XVZKSVPDJMENOS-UHFFFAOYSA-N 6-(2-chlorophenyl)-n'-methyl-n'-pyridin-2-yl-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbohydrazide Chemical compound C=1C=CC=NC=1N(C)NC(=O)C(=C1N=CC=2C=3C(=CC=CC=3)Cl)C=NN1C=2C1=CC=C(C(F)(F)F)C=C1 XVZKSVPDJMENOS-UHFFFAOYSA-N 0.000 claims 1
- ZBPBUSMUBCVXRS-UHFFFAOYSA-N 6-(2-chlorophenyl)-n-(1,1-dioxothiolan-3-yl)-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)NC3CS(=O)(=O)CC3)C=NN12 ZBPBUSMUBCVXRS-UHFFFAOYSA-N 0.000 claims 1
- IAJPCDBQEUYANO-UHFFFAOYSA-N 6-(2-chlorophenyl)-n-(thiolan-3-yl)-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)NC3CSCC3)C=NN12 IAJPCDBQEUYANO-UHFFFAOYSA-N 0.000 claims 1
- FXRIQZOUWDFHJW-QGZVFWFLSA-N 6-(2-chlorophenyl)-n-[(3r)-1,1-dioxothiolan-3-yl]-2-methyl-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)N[C@H]3CS(=O)(=O)CC3)C(C)=NN2C=1C1=CC=C(C(F)(F)F)C=C1 FXRIQZOUWDFHJW-QGZVFWFLSA-N 0.000 claims 1
- ZBPBUSMUBCVXRS-MRXNPFEDSA-N 6-(2-chlorophenyl)-n-[(3r)-1,1-dioxothiolan-3-yl]-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)N[C@H]3CS(=O)(=O)CC3)C=NN12 ZBPBUSMUBCVXRS-MRXNPFEDSA-N 0.000 claims 1
- FXRIQZOUWDFHJW-KRWDZBQOSA-N 6-(2-chlorophenyl)-n-[(3s)-1,1-dioxothiolan-3-yl]-2-methyl-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)N[C@@H]3CS(=O)(=O)CC3)C(C)=NN2C=1C1=CC=C(C(F)(F)F)C=C1 FXRIQZOUWDFHJW-KRWDZBQOSA-N 0.000 claims 1
- ZBPBUSMUBCVXRS-INIZCTEOSA-N 6-(2-chlorophenyl)-n-[(3s)-1,1-dioxothiolan-3-yl]-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)N[C@@H]3CS(=O)(=O)CC3)C=NN12 ZBPBUSMUBCVXRS-INIZCTEOSA-N 0.000 claims 1
- KOIUPGHBBKSOTQ-UHFFFAOYSA-N 6-(2-chlorophenyl)-n-cyclopentyl-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)NC3CCCC3)C=NN12 KOIUPGHBBKSOTQ-UHFFFAOYSA-N 0.000 claims 1
- YFNVYUCOKJBWLA-UHFFFAOYSA-N 6-(2-chlorophenyl)-n-cyclopentyl-7-[6-(trifluoromethyl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NC(C(F)(F)F)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)NC3CCCC3)C=NN12 YFNVYUCOKJBWLA-UHFFFAOYSA-N 0.000 claims 1
- YBQYBRZFUGONSB-LJQANCHMSA-N 6-(2-cyanophenyl)-n-[(3r)-1,1-dioxothiolan-3-yl]-2-methyl-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(C#N)C=1C=1C=NC2=C(C(=O)N[C@H]3CS(=O)(=O)CC3)C(C)=NN2C=1C1=CC=C(C(F)(F)F)C=C1 YBQYBRZFUGONSB-LJQANCHMSA-N 0.000 claims 1
- YBQYBRZFUGONSB-IBGZPJMESA-N 6-(2-cyanophenyl)-n-[(3s)-1,1-dioxothiolan-3-yl]-2-methyl-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(C#N)C=1C=1C=NC2=C(C(=O)N[C@@H]3CS(=O)(=O)CC3)C(C)=NN2C=1C1=CC=C(C(F)(F)F)C=C1 YBQYBRZFUGONSB-IBGZPJMESA-N 0.000 claims 1
- QCCZEVFSOGOIIV-AWEZNQCLSA-N 7-(4-chloro-2-fluorophenyl)-6-(2-chlorophenyl)-n-[(3s)-1,1-dioxothiolan-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C=NC2=C(C(=O)N[C@@H]3CS(=O)(=O)CC3)C=NN12 QCCZEVFSOGOIIV-AWEZNQCLSA-N 0.000 claims 1
- CFSWGAGHUIJIFZ-UHFFFAOYSA-N 7-(4-chloro-2-fluorophenyl)-6-(2-cyanophenyl)-2-methyl-n-pyrrolidin-1-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(C#N)C=1C=1C=NC2=C(C(=O)NN3CCCC3)C(C)=NN2C=1C1=CC=C(Cl)C=C1F CFSWGAGHUIJIFZ-UHFFFAOYSA-N 0.000 claims 1
- FRXZFGDSHMDSSG-QGZVFWFLSA-N 7-(4-chloro-2-fluorophenyl)-6-(2-cyanophenyl)-n-[(3r)-1,1-dioxothiolan-3-yl]-2-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(C#N)C=1C=1C=NC2=C(C(=O)N[C@H]3CS(=O)(=O)CC3)C(C)=NN2C=1C1=CC=C(Cl)C=C1F FRXZFGDSHMDSSG-QGZVFWFLSA-N 0.000 claims 1
- IVAFRUITLYVAHY-UHFFFAOYSA-N 7-(4-chlorophenyl)-6-(2-cyano-4-fluorophenyl)-n-pyrrolidin-1-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound N#CC1=CC(F)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N2N=CC(C(=O)NN3CCCC3)=C2N=C1 IVAFRUITLYVAHY-UHFFFAOYSA-N 0.000 claims 1
- QYYINDOQCZMYHI-UHFFFAOYSA-N 7-(4-chlorophenyl)-6-(2-cyanophenyl)-2-methyl-n-piperidin-1-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(C#N)C=1C=1C=NC2=C(C(=O)NN3CCCCC3)C(C)=NN2C=1C1=CC=C(Cl)C=C1 QYYINDOQCZMYHI-UHFFFAOYSA-N 0.000 claims 1
- UALKPJTWGVEJDG-UHFFFAOYSA-N 7-(4-chlorophenyl)-6-(2-cyanophenyl)-2-methyl-n-pyrrolidin-1-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(C#N)C=1C=1C=NC2=C(C(=O)NN3CCCC3)C(C)=NN2C=1C1=CC=C(Cl)C=C1 UALKPJTWGVEJDG-UHFFFAOYSA-N 0.000 claims 1
- KCCKKEDESCVOQX-UHFFFAOYSA-N 7-(4-chlorophenyl)-6-(2-cyanophenyl)-N-piperidin-1-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)C#N)C=NC2=C(C(=O)NN3CCCCC3)C=NN12 KCCKKEDESCVOQX-UHFFFAOYSA-N 0.000 claims 1
- GDSDMRXNPQJDQB-UHFFFAOYSA-N 7-(4-chlorophenyl)-6-(2-cyanophenyl)-n',2-dimethyl-n'-pyridin-2-ylpyrazolo[1,5-a]pyrimidine-3-carbohydrazide Chemical compound C=1C=CC=NC=1N(C)NC(=O)C(=C1N=CC=2C=3C(=CC=CC=3)C#N)C(C)=NN1C=2C1=CC=C(Cl)C=C1 GDSDMRXNPQJDQB-UHFFFAOYSA-N 0.000 claims 1
- WGEXNLBGLFAEML-UHFFFAOYSA-N 7-(4-chlorophenyl)-6-(2-cyanophenyl)-n'-methyl-n'-pyridin-2-ylpyrazolo[1,5-a]pyrimidine-3-carbohydrazide Chemical compound C=1C=CC=NC=1N(C)NC(=O)C(=C1N=CC=2C=3C(=CC=CC=3)C#N)C=NN1C=2C1=CC=C(Cl)C=C1 WGEXNLBGLFAEML-UHFFFAOYSA-N 0.000 claims 1
- LHMKLSZYXKKNSQ-LJQANCHMSA-N 7-(4-chlorophenyl)-6-(2-cyanophenyl)-n-[(3r)-1,1-dioxothiolan-3-yl]-2-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=CC=C(C#N)C=1C=1C=NC2=C(C(=O)N[C@H]3CS(=O)(=O)CC3)C(C)=NN2C=1C1=CC=C(Cl)C=C1 LHMKLSZYXKKNSQ-LJQANCHMSA-N 0.000 claims 1
- ZAIADNGAMGBLCE-UHFFFAOYSA-N 7-(4-chlorophenyl)-6-(2-cyanophenyl)-n-pyrrolidin-1-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)C#N)C=NC2=C(C(=O)NN3CCCC3)C=NN12 ZAIADNGAMGBLCE-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004460 dihydrobenzooxazinyl group Chemical group O1N(CCC2=C1C=CC=C2)* 0.000 claims 1
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims 1
- 125000005434 dihydrobenzoxazinyl group Chemical group O1N(CCC2=C1C=CC=C2)* 0.000 claims 1
- 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 claims 1
- 125000004609 dihydroquinazolinyl group Chemical group N1(CN=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims 1
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 1
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims 1
- BPDFHGQJUGAQLI-UHFFFAOYSA-N n-[6-(2-chlorophenyl)-3-(dimethylaminocarbamoyl)-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-2-yl]acetamide Chemical compound C=1C=CC=C(Cl)C=1C=1C=NC2=C(C(=O)NN(C)C)C(NC(C)=O)=NN2C=1C1=CC=C(C(F)(F)F)C=C1 BPDFHGQJUGAQLI-UHFFFAOYSA-N 0.000 claims 1
- IOHXPMJKGNALKV-UHFFFAOYSA-N n-[6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-[[methyl(pyridin-2-yl)amino]carbamoyl]pyrazolo[1,5-a]pyrimidin-2-yl]acetamide Chemical compound C=1C=CC=NC=1N(C)NC(=O)C(=C1N=CC=2C=3C(=CC=CC=3)Cl)C(NC(C)=O)=NN1C=2C1=CC=C(Cl)C=C1 IOHXPMJKGNALKV-UHFFFAOYSA-N 0.000 claims 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 150000002926 oxygen Chemical class 0.000 claims 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 150000003463 sulfur Chemical class 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000005505 thiomorpholino group Chemical group 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 125000005033 thiopyranyl group Chemical group 0.000 claims 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims 1
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| JP2006151470 | 2006-05-31 | ||
| JP2006285609A JP4847275B2 (ja) | 2005-10-21 | 2006-10-20 | ピラゾロ［１，５−ａ］ピリミジン化合物 |
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| JP2008007493A JP2008007493A (ja) | 2008-01-17 |
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| JP4847275B2 JP4847275B2 (ja) | 2011-12-28 |
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Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| TW201345908A (zh) * | 2006-07-05 | 2013-11-16 | Mitsubishi Tanabe Pharma Corp | 吡唑并〔１，５-ａ〕嘧啶化合物 |
| RU2369600C1 (ru) * | 2008-01-24 | 2009-10-10 | Андрей Александрович Иващенко | ЗАМЕЩЕННЫЕ 4-СУЛЬФОНИЛ-ПИРАЗОЛЫ И 3-СУЛЬФОНИЛ-ПИРАЗОЛО[1,5-a]ПИРИМИДИНЫ - АНТАГОНИСТЫ СЕРОТОНИНОВЫХ5-HT6 РЕЦЕПТОРОВ, АКТИВНЫЙ КОМПОНЕНТ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, ЛЕКАРСТВЕННОЕ СРЕДСТВО И СПОСОБЫ ИХ ПОЛУЧЕНИЯ |
| CN102223798A (zh) * | 2008-09-24 | 2011-10-19 | 巴斯夫欧洲公司 | 用于防治无脊椎动物害虫的吡唑化合物 |
| EA024353B1 (ru) * | 2010-07-29 | 2016-09-30 | Астеллас Фарма Инк. | Конденсированные циклические соединения пиридина |
| EP2834243B1 (en) * | 2012-03-09 | 2018-04-25 | Lexicon Pharmaceuticals, Inc. | PYRAZOLO[1,5-a]PYRIMIDINE-BASED COMPOUNDS, COMPOSITIONS COMPRISING THEM, AND METHODS OF THEIR USE |
| TW201542550A (zh) * | 2013-09-06 | 2015-11-16 | Lexicon Pharmaceuticals Inc | 吡唑并［１，５－ａ］嘧啶基化合物、包含彼之組合物以及使用彼之方法 |
| EP3156405A1 (en) | 2015-10-13 | 2017-04-19 | Boehringer Ingelheim International GmbH | Spirocyclic ether derivatives of pyrazolo[1,5-a]pyrimidine-3-carboxamide |
| WO2018093698A1 (en) * | 2016-11-18 | 2018-05-24 | Merck Sharp & Dohme Corp. | Indole derivatives useful as inhibitors of diacylglyceride o-acyltransferase 2 |
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| US7196111B2 (en) * | 2002-06-04 | 2007-03-27 | Schering Corporation | Pyrazolo[1,5a]pyrimidine compounds as antiviral agents |
| US7329658B2 (en) * | 2003-02-06 | 2008-02-12 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| US7176210B2 (en) * | 2003-02-10 | 2007-02-13 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
| DE102004008807A1 (de) * | 2004-02-20 | 2005-09-08 | Bayer Cropscience Ag | Pyrazolopyrimidine |
| WO2005103052A1 (en) * | 2004-04-21 | 2005-11-03 | Pfizer Products Inc. | Pyrazolo [1,5-a] pyrimidin-7-one compounds and uses thereof |
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