JP2006522749A5 - - Google Patents
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- JP2006522749A5 JP2006522749A5 JP2006504356A JP2006504356A JP2006522749A5 JP 2006522749 A5 JP2006522749 A5 JP 2006522749A5 JP 2006504356 A JP2006504356 A JP 2006504356A JP 2006504356 A JP2006504356 A JP 2006504356A JP 2006522749 A5 JP2006522749 A5 JP 2006522749A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazolo
- pyrimidin
- ethanone
- trifluoromethyl
- phenyl
- 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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- -1 C 1 -C 6 alkyl Chemical group 0.000 claims 340
- 125000003118 aryl group Chemical group 0.000 claims 69
- 125000001072 heteroaryl group Chemical group 0.000 claims 50
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims 26
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- 239000008194 pharmaceutical composition Substances 0.000 claims 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 18
- 150000002431 hydrogen Chemical class 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 17
- 239000000203 mixture Substances 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 14
- 230000003287 optical effect Effects 0.000 claims 14
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 238000004519 manufacturing process Methods 0.000 claims 13
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 12
- 125000004043 oxo group Chemical group O=* 0.000 claims 11
- 208000002705 Glucose Intolerance Diseases 0.000 claims 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 201000010099 disease Diseases 0.000 claims 9
- 208000035475 disorder Diseases 0.000 claims 9
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 9
- 201000009104 prediabetes syndrome Diseases 0.000 claims 9
- 230000002265 prevention Effects 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000004953 trihalomethyl group Chemical group 0.000 claims 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 239000002253 acid Substances 0.000 claims 7
- 230000000694 effects Effects 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 7
- 239000000651 prodrug Chemical class 0.000 claims 7
- 229940002612 prodrug Drugs 0.000 claims 7
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 claims 7
- 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 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 6
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 125000004951 trihalomethoxy group Chemical group 0.000 claims 5
- 206010056997 Impaired fasting glucose Diseases 0.000 claims 4
- JFUAWXPBHXKZGA-IBGZPJMESA-N 4-fluoro-2-[(4r)-5,5,5-trifluoro-4-hydroxy-2-methyl-4-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-yl]phenol Chemical compound C([C@@](O)(CC=1NC2=CN=CC=C2C=1)C(F)(F)F)C(C)(C)C1=CC(F)=CC=C1O JFUAWXPBHXKZGA-IBGZPJMESA-N 0.000 claims 3
- 208000032928 Dyslipidaemia Diseases 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 206010020772 Hypertension Diseases 0.000 claims 3
- 206010022489 Insulin Resistance Diseases 0.000 claims 3
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 230000002411 adverse Effects 0.000 claims 3
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 239000003862 glucocorticoid Substances 0.000 claims 3
- 229940124750 glucocorticoid receptor agonist Drugs 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 230000005764 inhibitory process Effects 0.000 claims 3
- 230000003834 intracellular effect Effects 0.000 claims 3
- QTSHYHWZCCQNPO-UHFFFAOYSA-N n-cyclohexyl-n,5-dimethyl-7-phenylpyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C)C=C(C=3C=CC=CC=3)N2N=C1C(=O)N(C)C1CCCCC1 QTSHYHWZCCQNPO-UHFFFAOYSA-N 0.000 claims 3
- INDCEILCISRFBY-UHFFFAOYSA-N n-cyclohexyl-n-methyl-5,7-diphenylpyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C=3C=CC=CC=3)C=C(C=3C=CC=CC=3)N2N=C1C(=O)N(C)C1CCCCC1 INDCEILCISRFBY-UHFFFAOYSA-N 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Chemical group 0.000 claims 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 3
- 238000002560 therapeutic procedure Methods 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- YRVQVNYRNOTDSR-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)-n-cyclohexyl-n-methyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)(F)F)=CC(C=3C=C4OCOC4=CC=3)=NC2=C1C(=O)N(C)C1CCCCC1 YRVQVNYRNOTDSR-UHFFFAOYSA-N 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 230000005856 abnormality Effects 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 230000009286 beneficial effect Effects 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- YJBSMVLFICCSJH-UHFFFAOYSA-N n-benzyl-5-(4-methoxyphenyl)-n-methyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(C(=O)N(C)CC=3C=CC=CC=3)C=NN2C(C(F)(F)F)=C1 YJBSMVLFICCSJH-UHFFFAOYSA-N 0.000 claims 2
- KHINXPVHPGLZMC-UHFFFAOYSA-N n-benzyl-n-methyl-5-thiophen-2-yl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)(F)F)=CC(C=3SC=CC=3)=NC2=C1C(=O)N(C)CC1=CC=CC=C1 KHINXPVHPGLZMC-UHFFFAOYSA-N 0.000 claims 2
- MBAKXDICUHOJFX-UHFFFAOYSA-N n-cyclohexyl-n,5-dimethyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C)C=C(C(F)(F)F)N2N=C1C(=O)N(C)C1CCCCC1 MBAKXDICUHOJFX-UHFFFAOYSA-N 0.000 claims 2
- ZOKLERDPZFUYDM-UHFFFAOYSA-N n-cyclohexyl-n,7-dimethyl-5-phenylpyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C=3C=CC=CC=3)C=C(C)N2N=C1C(=O)N(C)C1CCCCC1 ZOKLERDPZFUYDM-UHFFFAOYSA-N 0.000 claims 2
- BUMFOISZBMNSJG-UHFFFAOYSA-N n-cyclohexyl-n-methyl-5-naphthalen-1-yl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C=3C4=CC=CC=C4C=CC=3)C=C(C(F)(F)F)N2N=C1C(=O)N(C)C1CCCCC1 BUMFOISZBMNSJG-UHFFFAOYSA-N 0.000 claims 2
- PKDPOEUUQXIGBU-UHFFFAOYSA-N n-cyclohexyl-n-methyl-7-phenyl-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C(F)(F)F)C=C(C=3C=CC=CC=3)N2N=C1C(=O)N(C)C1CCCCC1 PKDPOEUUQXIGBU-UHFFFAOYSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 238000007911 parenteral administration Methods 0.000 claims 2
- 230000002685 pulmonary effect Effects 0.000 claims 2
- IGXOTVNZNQOWEC-UHFFFAOYSA-N 1-[7-(difluoromethyl)-5-methylpyrazolo[1,5-a]pyrimidine-3-carbonyl]piperidine-4-carboxamide Chemical compound C=12N=C(C)C=C(C(F)F)N2N=CC=1C(=O)N1CCC(C(N)=O)CC1 IGXOTVNZNQOWEC-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- MXPUPKZRQSPLBY-UHFFFAOYSA-N 3-bromo-5-(4-bromophenyl)-n-cyclohexyl-n-methyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound N=1N2C(C(F)(F)F)=CC(C=3C=CC(Br)=CC=3)=NC2=C(Br)C=1C(=O)N(C)C1CCCCC1 MXPUPKZRQSPLBY-UHFFFAOYSA-N 0.000 claims 1
- CTXXXHCJUJZTKC-UHFFFAOYSA-N 3-bromo-n-cyclohexyl-5-(furan-2-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound N=1N2C(C(F)(F)F)=CC(C=3OC=CC=3)=NC2=C(Br)C=1C(=O)NC1CCCCC1 CTXXXHCJUJZTKC-UHFFFAOYSA-N 0.000 claims 1
- SPCUVPOVZSGXTC-UHFFFAOYSA-N 3-bromo-n-cyclohexyl-n-methyl-5-thiophen-2-yl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound N=1N2C(C(F)(F)F)=CC(C=3SC=CC=3)=NC2=C(Br)C=1C(=O)N(C)C1CCCCC1 SPCUVPOVZSGXTC-UHFFFAOYSA-N 0.000 claims 1
- LHOPHTDOMJORCU-UHFFFAOYSA-N 3-chloro-5-(4-methoxyphenyl)-n-methyl-n-(2-pyridin-2-ylethyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(Cl)C(C(=O)N(C)CCC=3N=CC=CC=3)=NN2C(C(F)(F)F)=C1 LHOPHTDOMJORCU-UHFFFAOYSA-N 0.000 claims 1
- LMQVACPEALDOMF-UHFFFAOYSA-N 3-chloro-n-[(1,3-dimethylpyrazol-4-yl)methyl]-5-(4-methoxyphenyl)-n-methyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(Cl)C(C(=O)N(C)CC=3C(=NN(C)C=3)C)=NN2C(C(F)(F)F)=C1 LMQVACPEALDOMF-UHFFFAOYSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- APPISXLWZYHSDY-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC2=CC(C(O)=O)=NN2C(C(F)(F)F)=C1 APPISXLWZYHSDY-UHFFFAOYSA-N 0.000 claims 1
- WKEDRUYMPCCRMF-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-[(1,3-dimethylpyrazol-4-yl)methyl]-n-methyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C=3C=CC(Cl)=CC=3)C=C(C(F)(F)F)N2N=C1C(=O)N(C)CC1=CN(C)N=C1C WKEDRUYMPCCRMF-UHFFFAOYSA-N 0.000 claims 1
- BSIUFDZZYXKSRS-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-[(1,5-dimethylpyrazol-4-yl)methyl]-n-methyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C=3C=CC(Cl)=CC=3)C=C(C(F)(F)F)N2N=C1C(=O)N(C)CC=1C=NN(C)C=1C BSIUFDZZYXKSRS-UHFFFAOYSA-N 0.000 claims 1
- IZYULJPASQYGFY-UHFFFAOYSA-N 5-(furan-2-yl)-n-methyl-7-(trifluoromethyl)-n-[(1,3,5-trimethylpyrazol-4-yl)methyl]pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C=3OC=CC=3)C=C(C(F)(F)F)N2N=C1C(=O)N(C)CC=1C(C)=NN(C)C=1C IZYULJPASQYGFY-UHFFFAOYSA-N 0.000 claims 1
- FRVNEDJZGFPOOY-UHFFFAOYSA-N 7-(difluoromethyl)-n-[(1-ethyl-3-methylpyrazol-4-yl)methyl]-5-(4-methoxyphenyl)-n-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1=NN(CC)C=C1CN(C)C(=O)C1=C2N=C(C=3C=CC(OC)=CC=3)C=C(C(F)F)N2N=C1 FRVNEDJZGFPOOY-UHFFFAOYSA-N 0.000 claims 1
- RUNBGQGFOAAVCJ-UHFFFAOYSA-N 7-(difluoromethyl)-n-[(1-ethyl-3-methylpyrazol-4-yl)methyl]-n-methyl-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1=NN(CC)C=C1CN(C)C(=O)C1=C2N=C(C=3C=CC=CC=3)C=C(C(F)F)N2N=C1 RUNBGQGFOAAVCJ-UHFFFAOYSA-N 0.000 claims 1
- DFWYLVSJBBCXND-UHFFFAOYSA-N 7-(difluoromethyl)-n-[(1-ethyl-5-methylpyrazol-4-yl)methyl]-n-methyl-5-(4-methylphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CCN1N=CC(CN(C)C(=O)C2=C3N=C(C=C(N3N=C2)C(F)F)C=2C=CC(C)=CC=2)=C1C DFWYLVSJBBCXND-UHFFFAOYSA-N 0.000 claims 1
- HQQYSYGDZZFZDL-UHFFFAOYSA-N 7-(difluoromethyl)-n-methyl-5-(4-methylphenyl)-n-[(1-methylpyrazol-4-yl)methyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)F)=CC(C=3C=CC(C)=CC=3)=NC2=C1C(=O)N(C)CC=1C=NN(C)C=1 HQQYSYGDZZFZDL-UHFFFAOYSA-N 0.000 claims 1
- LMBLGFDIFWDELY-UHFFFAOYSA-N 7-(difluoromethyl)-n-methyl-5-phenyl-n-[(1,3,5-trimethylpyrazol-4-yl)methyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)F)=CC(C=3C=CC=CC=3)=NC2=C1C(=O)N(C)CC=1C(C)=NN(C)C=1C LMBLGFDIFWDELY-UHFFFAOYSA-N 0.000 claims 1
- QNZOQXJQJXUQDO-UHFFFAOYSA-N 7-(difluoromethyl)-n-methyl-5-phenyl-n-[(4-pyrazol-1-ylphenyl)methyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)F)=CC(C=3C=CC=CC=3)=NC2=C1C(=O)N(C)CC(C=C1)=CC=C1N1C=CC=N1 QNZOQXJQJXUQDO-UHFFFAOYSA-N 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- ZZFOXLVCTUQYFO-UHFFFAOYSA-N C1(CCCCC1)N(C(=O)C1=NC=CC=N1)C Chemical compound C1(CCCCC1)N(C(=O)C1=NC=CC=N1)C ZZFOXLVCTUQYFO-UHFFFAOYSA-N 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- BNTSRVOXNJXPQO-UHFFFAOYSA-N [5-(1,3-benzodioxol-5-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]-piperazin-1-ylmethanone Chemical compound O1COC2=C1C=CC(=C2)C1=NC=2N(C(=C1)C(F)(F)F)N=C(C=2)C(=O)N1CCNCC1 BNTSRVOXNJXPQO-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 230000007123 defense Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- ZINWADPKZHBBEQ-UHFFFAOYSA-N ethyl 1-[5-(3-methoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carbonyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)C1=C2N=C(C=3C=C(OC)C=CC=3)C=C(C(F)(F)F)N2N=C1 ZINWADPKZHBBEQ-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- VXHWOJNPZOKEHB-UHFFFAOYSA-N methyl 5-methyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxylate Chemical compound N1=C(C)C=C(C(F)(F)F)N2N=C(C(=O)OC)C=C21 VXHWOJNPZOKEHB-UHFFFAOYSA-N 0.000 claims 1
- JMOYKIQMZUYRLO-UHFFFAOYSA-N methyl 5-methyl-7-phenylpyrazolo[1,5-a]pyrimidine-2-carboxylate Chemical compound N12N=C(C(=O)OC)C=C2N=C(C)C=C1C1=CC=CC=C1 JMOYKIQMZUYRLO-UHFFFAOYSA-N 0.000 claims 1
- QPCZVFDRLFBYKQ-UHFFFAOYSA-N methyl 7-methyl-5-phenylpyrazolo[1,5-a]pyrimidine-2-carboxylate Chemical compound C1=C(C)N2N=C(C(=O)OC)C=C2N=C1C1=CC=CC=C1 QPCZVFDRLFBYKQ-UHFFFAOYSA-N 0.000 claims 1
- DOOAYMMDWWIAJQ-UHFFFAOYSA-N n-[(1,3-dimethylpyrazol-4-yl)methyl]-n-methyl-5-(4-methylphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)(F)F)=CC(C=3C=CC(C)=CC=3)=NC2=C1C(=O)N(C)CC1=CN(C)N=C1C DOOAYMMDWWIAJQ-UHFFFAOYSA-N 0.000 claims 1
- NLFJLMOIXJFXNH-UHFFFAOYSA-N n-[(1,3-dimethylpyrazol-4-yl)methyl]-n-methyl-5-phenyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C=3C=CC=CC=3)C=C(C(F)(F)F)N2N=C1C(=O)N(C)CC1=CN(C)N=C1C NLFJLMOIXJFXNH-UHFFFAOYSA-N 0.000 claims 1
- PJWUAFNNTFUQEE-UHFFFAOYSA-N n-[(1,5-dimethylpyrazol-4-yl)methyl]-n-methyl-5-thiophen-2-yl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C=3SC=CC=3)C=C(C(F)(F)F)N2N=C1C(=O)N(C)CC=1C=NN(C)C=1C PJWUAFNNTFUQEE-UHFFFAOYSA-N 0.000 claims 1
- UNWUKCQLINQLAH-UHFFFAOYSA-N n-benzyl-7-(difluoromethyl)-n-methyl-5-(4-methylphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)F)=CC(C=3C=CC(C)=CC=3)=NC2=C1C(=O)N(C)CC1=CC=CC=C1 UNWUKCQLINQLAH-UHFFFAOYSA-N 0.000 claims 1
- XGFAPUQEUDMPLY-UHFFFAOYSA-N n-benzyl-n,7-dimethyl-5-phenylpyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C=3C=CC=CC=3)C=C(C)N2N=C1C(=O)N(C)CC1=CC=CC=C1 XGFAPUQEUDMPLY-UHFFFAOYSA-N 0.000 claims 1
- CQQMWVSZEXOCFU-UHFFFAOYSA-N n-benzyl-n-(2-hydroxyethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C=CC=NC2=C1C(=O)N(CCO)CC1=CC=CC=C1 CQQMWVSZEXOCFU-UHFFFAOYSA-N 0.000 claims 1
- ZJSWTFDCYDLVHN-UHFFFAOYSA-N n-benzyl-n-methyl-5,7-diphenylpyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C=3C=CC=CC=3)C=C(C=3C=CC=CC=3)N2N=C1C(=O)N(C)CC1=CC=CC=C1 ZJSWTFDCYDLVHN-UHFFFAOYSA-N 0.000 claims 1
- NFXCDSGIARGWGR-UHFFFAOYSA-N n-benzyl-n-methyl-5-phenyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C=3C=CC=CC=3)C=C(C(F)(F)F)N2N=C1C(=O)N(C)CC1=CC=CC=C1 NFXCDSGIARGWGR-UHFFFAOYSA-N 0.000 claims 1
- KTNVTWJULHUMIG-UHFFFAOYSA-N n-cyclohexyl-5,7-diphenylpyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C=3C=CC=CC=3)C=C(C=3C=CC=CC=3)N2N=C1C(=O)NC1CCCCC1 KTNVTWJULHUMIG-UHFFFAOYSA-N 0.000 claims 1
- NFVRQXKVUIOORT-UHFFFAOYSA-N n-cyclohexyl-5-(4-ethoxyphenyl)-7-methylpyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=CC(OCC)=CC=C1C1=NC2=CC(C(=O)NC3CCCCC3)=NN2C(C)=C1 NFVRQXKVUIOORT-UHFFFAOYSA-N 0.000 claims 1
- ZVARSEGSFLYPKC-UHFFFAOYSA-N n-cyclohexyl-5-methyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C)C=C(C(F)(F)F)N2N=C1C(=O)NC1CCCCC1 ZVARSEGSFLYPKC-UHFFFAOYSA-N 0.000 claims 1
- WJGXYRKNJCXIBJ-UHFFFAOYSA-N n-cyclohexyl-5-methyl-7-phenylpyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound N12N=C(C(=O)NC3CCCCC3)C=C2N=C(C)C=C1C1=CC=CC=C1 WJGXYRKNJCXIBJ-UHFFFAOYSA-N 0.000 claims 1
- XDGANCLEDCXFPK-UHFFFAOYSA-N n-cyclohexyl-5-naphthalen-1-yl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound N=1N2C(C(F)(F)F)=CC(C=3C4=CC=CC=C4C=CC=3)=NC2=CC=1C(=O)NC1CCCCC1 XDGANCLEDCXFPK-UHFFFAOYSA-N 0.000 claims 1
- IEAUSQAYZSMWJB-UHFFFAOYSA-N n-cyclohexyl-5-phenyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)(F)F)=CC(C=3C=CC=CC=3)=NC2=C1C(=O)NC1CCCCC1 IEAUSQAYZSMWJB-UHFFFAOYSA-N 0.000 claims 1
- NLLNTKSMRZHNFE-UHFFFAOYSA-N n-cyclohexyl-n-methyl-5-thiophen-2-yl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C=3SC=CC=3)C=C(C(F)(F)F)N2N=C1C(=O)N(C)C1CCCCC1 NLLNTKSMRZHNFE-UHFFFAOYSA-N 0.000 claims 1
- XVSLMQJRPBLXDK-UHFFFAOYSA-N n-cyclohexylpyrimidine-2-carboxamide Chemical compound N=1C=CC=NC=1C(=O)NC1CCCCC1 XVSLMQJRPBLXDK-UHFFFAOYSA-N 0.000 claims 1
- XIKRWCSDOFPIMD-UHFFFAOYSA-N n-methyl-5-(4-methylphenyl)-7-(trifluoromethyl)-n-[(1,3,5-trimethylpyrazol-4-yl)methyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)(F)F)=CC(C=3C=CC(C)=CC=3)=NC2=C1C(=O)N(C)CC=1C(C)=NN(C)C=1C XIKRWCSDOFPIMD-UHFFFAOYSA-N 0.000 claims 1
- WBVHYTOOZVAPLB-UHFFFAOYSA-N n-methyl-5-thiophen-2-yl-7-(trifluoromethyl)-n-[(1,3,5-trimethylpyrazol-4-yl)methyl]pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C=3SC=CC=3)C=C(C(F)(F)F)N2N=C1C(=O)N(C)CC=1C(C)=NN(C)C=1C WBVHYTOOZVAPLB-UHFFFAOYSA-N 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 0 *c1c2nc(*)c(*)c(*)[n]2nc1* Chemical compound *c1c2nc(*)c(*)c(*)[n]2nc1* 0.000 description 1
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| US46745303P | 2003-05-02 | 2003-05-02 | |
| PCT/DK2004/000253 WO2004089471A2 (en) | 2003-04-11 | 2004-04-06 | NEW PYRAZOLO[1,5-a] PYRIMIDINES DERIVATIVES AND PHARMACEUTICAL USE THEREOF |
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| JP2006522749A JP2006522749A (ja) | 2006-10-05 |
| JP2006522749A5 true JP2006522749A5 (https=) | 2007-05-31 |
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| EP (1) | EP1615697A2 (https=) |
| JP (1) | JP2006522749A (https=) |
| WO (1) | WO2004089471A2 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12336982B2 (en) | 2018-11-21 | 2025-06-24 | Rodeo Therapeutics Corporation | Compositions and methods of modulating short-chain dehydrogenase activity |
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| BRPI0710479A2 (pt) | 2006-01-18 | 2012-08-14 | Hoffmann La Roche | composto, processo para sua preparaÇço, composiÇço farmacÊutica, uso de um composto e mÉtodo de tratamento de doenÇa ou desosrdem metabàlica. |
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| EP2683701B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
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| PL3177624T3 (pl) | 2014-08-06 | 2019-09-30 | Pfizer Inc. | Związki imidazopirydazynowe |
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| JOP20190213A1 (ar) | 2017-03-16 | 2019-09-16 | Array Biopharma Inc | مركبات حلقية ضخمة كمثبطات لكيناز ros1 |
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| JP2023132740A (ja) * | 2022-03-11 | 2023-09-22 | ナショナル ヘルス リサーチ インスティテューツ | Ｐｔｇｒ２阻害物質及びそれらの使用 |
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| AU557300B2 (en) * | 1982-03-16 | 1986-12-18 | Farmitalia Carlo Erba S.P.A. | Substituted 1h-pyrazolo(1,5-alpha)pyrimidines and processes for their preparation |
| US5169850A (en) * | 1990-01-22 | 1992-12-08 | American Cyanamid Company | N-(dialkylamino)methylene)-substituted pyrazolo(1,5-a)-pyrimidine-3-carboxamides and N-(dialkylamino)methylene-substituted-4,5-dihydropyrazolo-(1,5-a)-pyrimidine-3-carboxamides |
| US5571813A (en) * | 1993-06-10 | 1996-11-05 | Beiersdorf-Lilly Gmbh | Fused pyrimidine compounds and their use as pharmaceuticals |
| US6124289A (en) * | 1996-07-24 | 2000-09-26 | Dupont Pharmaceuticals Co. | Azolo triazines and pyrimidines |
| JP2002053466A (ja) * | 2000-08-08 | 2002-02-19 | Otsuka Pharmaceut Factory Inc | アポトーシス調整剤 |
| JP2002212076A (ja) * | 2000-11-17 | 2002-07-31 | Ishihara Sangyo Kaisha Ltd | 縮合複素環化合物またはその塩を含有する糖尿病の予防または治療薬 |
| JP2003286171A (ja) * | 2002-03-28 | 2003-10-07 | Sumitomo Pharmaceut Co Ltd | Ｐａｒ阻害剤 |
-
2004
- 2004-04-06 WO PCT/DK2004/000253 patent/WO2004089471A2/en not_active Ceased
- 2004-04-06 EP EP04725889A patent/EP1615697A2/en not_active Withdrawn
- 2004-04-06 JP JP2006504356A patent/JP2006522749A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12336982B2 (en) | 2018-11-21 | 2025-06-24 | Rodeo Therapeutics Corporation | Compositions and methods of modulating short-chain dehydrogenase activity |
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