JP2006522749A5 - - Google Patents
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- Publication number
- 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 hetcycloalkyl Chemical group 0.000 claims 327
- 125000000217 alkyl group Chemical group 0.000 claims 91
- 125000003118 aryl group Chemical group 0.000 claims 66
- 125000003545 alkoxy group Chemical group 0.000 claims 51
- 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
- 125000005157 alkyl carboxy group Chemical group 0.000 claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- 239000008194 pharmaceutical composition Substances 0.000 claims 19
- 201000010099 disease 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 Effects 0.000 claims 14
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 13
- 238000004519 manufacturing process Methods 0.000 claims 13
- 125000004043 oxo group Chemical group O=* 0.000 claims 11
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 10
- 208000002705 Glucose Intolerance Diseases 0.000 claims 9
- 208000001072 Type 2 Diabetes Mellitus Diseases 0.000 claims 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 9
- 230000002265 prevention Effects 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 239000011780 sodium chloride Substances 0.000 claims 9
- 125000004953 trihalomethyl group Chemical group 0.000 claims 9
- TUCNEACPLKLKNU-UHFFFAOYSA-N ethanone Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims 8
- 239000002253 acid Substances 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 prodrugs 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
- 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
- 125000004183 alkoxy alkyl 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
- 125000004951 trihalomethoxy group Chemical group 0.000 claims 5
- 206010056997 Impaired fasting glucose Diseases 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- 230000002401 inhibitory effect Effects 0.000 claims 4
- 230000000051 modifying Effects 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
- 206010058108 Dyslipidaemia Diseases 0.000 claims 3
- 206010020772 Hypertension Diseases 0.000 claims 3
- 206010022489 Insulin resistance Diseases 0.000 claims 3
- 206010061227 Lipid metabolism disease Diseases 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
- 208000008589 Obesity Diseases 0.000 claims 3
- 125000005418 aryl aryl group Chemical group 0.000 claims 3
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 125000004432 carbon atoms Chemical group C* 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 239000003862 glucocorticoid Substances 0.000 claims 3
- 125000005842 heteroatoms Chemical group 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 230000003834 intracellular Effects 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
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 3
- 238000002560 therapeutic procedure Methods 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 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
- 206010003210 Arteriosclerosis Diseases 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 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
- 125000005024 alkenyl aryl group Chemical group 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000005025 alkynylaryl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 235000020828 fasting Nutrition 0.000 claims 2
- 239000008103 glucose Substances 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 Effects 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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
- 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
- XPEJXIXVBXJDGH-UHFFFAOYSA-N 3-chloro-N-cyclohexyl-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)C3CCCCC3)=NN2C(C(F)(F)F)=C1 XPEJXIXVBXJDGH-UHFFFAOYSA-N 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
- RGXXINUDDDUIGP-UHFFFAOYSA-N CN1N=C(C(=C1)C[N-]C)C.C1(=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O)C Chemical compound CN1N=C(C(=C1)C[N-]C)C.C1(=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O)C RGXXINUDDDUIGP-UHFFFAOYSA-N 0.000 claims 1
- 208000008787 Cardiovascular Disease Diseases 0.000 claims 1
- 206010012601 Diabetes mellitus Diseases 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
- BNTSRVOXNJXPQO-UHFFFAOYSA-N O1COC2=C1C=CC(=C2)C1=NC=2N(C(=C1)C(F)(F)F)N=C(C=2)C(=O)N1CCNCC1 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
- 206010037175 Psychiatric disease Diseases 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 201000001320 atherosclerosis Diseases 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 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
- 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
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000000546 pharmaceutic aid Substances 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 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 (sh) | 2007-05-31 |
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| JP2006504356A Pending JP2006522749A (ja) | 2003-04-11 | 2004-04-06 | 置換ピラゾロ［１，５−ａ］ピリミジンの薬学的使用 |
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| EP (1) | EP1615697A2 (sh) |
| JP (1) | JP2006522749A (sh) |
| WO (1) | WO2004089471A2 (sh) |
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| NZ555966A (en) | 2005-01-05 | 2011-03-31 | Abbott Lab | Adamantyl derivatives as inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
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| EP2527337A1 (en) * | 2005-04-14 | 2012-11-28 | Bristol-Myers Squibb Company | Inhibitors of 11-beta hydroxysteroid dehydrogenase type I |
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| RU2450004C2 (ru) * | 2006-08-04 | 2012-05-10 | Мерц Фарма Гмбх Унд Ко. Кгаа | Замещенные пиразолопиримидины, способ их получения и их применение в качестве лекарственного средства |
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| UA121658C2 (uk) | 2014-05-23 | 2020-07-10 | Ф. Хоффманн-Ля Рош Аг | Сполуки 5-хлордифторметоксифенілпіразолопіримідину як інгібітори янус-кінази |
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| JP7061602B2 (ja) | 2016-04-04 | 2022-04-28 | ロクソ オンコロジー， インコーポレイテッド | （Ｓ）－Ｎ－（５－（（Ｒ）－２－（２，５－ジフルオロフェニル）－ピロリジン－１－イル）－ピラゾロ［１，５－ａ］ピリミジン－３－イル）－３－ヒドロキシピロリジン－１－カルボキサミドの液体製剤 |
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| US11690847B2 (en) | 2016-11-30 | 2023-07-04 | Case Western Reserve University | Combinations of 15-PGDH inhibitors with corticosteroids and/or TNF inhibitors and uses thereof |
| WO2018145080A1 (en) * | 2017-02-06 | 2018-08-09 | Case Western Reserve University | Compositions and methods of modulating short-chain dehydrogenase activity |
| JOP20190213A1 (ar) | 2017-03-16 | 2019-09-16 | Array Biopharma Inc | مركبات حلقية ضخمة كمثبطات لكيناز ros1 |
| US11426420B2 (en) | 2017-04-07 | 2022-08-30 | Case Western Reserve University | Inhibitors of short-chain dehydrogenase activity for treating coronary disorders |
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| CN116348468A (zh) | 2020-10-23 | 2023-06-27 | 日东制药株式会社 | Cftr调节剂化合物、组合物及其用途 |
| AU2022285372A1 (en) * | 2021-06-02 | 2023-11-30 | Otsuka Pharmaceutical Co., Ltd. | Pyrazolo[1,5-a]pyrimidine compound for the treatment of dermal disorders |
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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 active Application Filing
- 2004-04-06 EP EP04725889A patent/EP1615697A2/en not_active Withdrawn
- 2004-04-06 JP JP2006504356A patent/JP2006522749A/ja active Pending
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