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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| 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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| JP (1) | JP2006522749A (enExample) |
| WO (1) | WO2004089471A2 (enExample) |
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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| 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 |
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| JP2003286171A (ja) * | 2002-03-28 | 2003-10-07 | Sumitomo Pharmaceut Co Ltd | Ｐａｒ阻害剤 |
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- 2004-04-06 EP EP04725889A patent/EP1615697A2/en not_active Withdrawn
- 2004-04-06 JP JP2006504356A patent/JP2006522749A/ja active Pending
- 2004-04-06 WO PCT/DK2004/000253 patent/WO2004089471A2/en not_active Ceased
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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