JP2006522749A - 置換ピラゾロ［１，５−ａ］ピリミジンの薬学的使用 - Google Patents
置換ピラゾロ［１，５−ａ］ピリミジンの薬学的使用 Download PDFInfo
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- JP2006522749A JP2006522749A JP2006504356A JP2006504356A JP2006522749A JP 2006522749 A JP2006522749 A JP 2006522749A JP 2006504356 A JP2006504356 A JP 2006504356A JP 2006504356 A JP2006504356 A JP 2006504356A JP 2006522749 A JP2006522749 A JP 2006522749A
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- JP
- Japan
- Prior art keywords
- pyrazolo
- pyrimidin
- ethanone
- trifluoromethyl
- methyl
- 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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- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 150000001875 compounds Chemical class 0.000 claims abstract description 136
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 53
- 238000011282 treatment Methods 0.000 claims abstract description 46
- 230000000694 effects Effects 0.000 claims abstract description 43
- 238000004519 manufacturing process Methods 0.000 claims abstract description 28
- 239000003862 glucocorticoid Substances 0.000 claims abstract description 21
- 230000002265 prevention Effects 0.000 claims abstract description 19
- 239000003814 drug Substances 0.000 claims abstract description 16
- 230000003834 intracellular effect Effects 0.000 claims abstract description 13
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 579
- 125000003118 aryl group Chemical group 0.000 claims description 153
- 125000001072 heteroaryl group Chemical group 0.000 claims description 110
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 65
- 239000000203 mixture Substances 0.000 claims description 60
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 54
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 40
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 38
- 201000010099 disease Diseases 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 229940002612 prodrug Drugs 0.000 claims description 33
- 239000000651 prodrug Chemical class 0.000 claims description 33
- 208000035475 disorder Diseases 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 29
- 230000003287 optical effect Effects 0.000 claims description 29
- 229940124750 glucocorticoid receptor agonist Drugs 0.000 claims description 27
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 25
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 23
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 23
- 125000004043 oxo group Chemical group O=* 0.000 claims description 23
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 22
- 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 description 21
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 19
- 208000008589 Obesity Diseases 0.000 claims description 18
- 235000020824 obesity Nutrition 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000001301 oxygen Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 206010022489 Insulin Resistance Diseases 0.000 claims description 13
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 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 description 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
- 206010020772 Hypertension Diseases 0.000 claims description 12
- 206010056997 Impaired fasting glucose Diseases 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 206010012601 diabetes mellitus Diseases 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 125000004951 trihalomethoxy group Chemical group 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 10
- 125000002619 bicyclic group Chemical group 0.000 claims description 9
- 230000005764 inhibitory process Effects 0.000 claims description 9
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 8
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 230000009286 beneficial effect Effects 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000002552 dosage form Substances 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 230000002411 adverse Effects 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 208000020016 psychiatric disease Diseases 0.000 claims description 6
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 230000005856 abnormality Effects 0.000 claims description 5
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 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 description 5
- 230000004770 neurodegeneration Effects 0.000 claims description 5
- 238000007911 parenteral administration Methods 0.000 claims description 5
- 230000002685 pulmonary effect Effects 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 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 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
- 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 description 3
- 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 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 9
- 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
- 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
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 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
- 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
- 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
- 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
- 230000007123 defense Effects 0.000 claims 1
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- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- 239000002562 thickening agent Substances 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
- 229960004605 timolol Drugs 0.000 description 1
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- OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
- GYHCTFXIZSNGJT-UHFFFAOYSA-N tolvaptan Chemical compound CC1=CC=CC=C1C(=O)NC(C=C1C)=CC=C1C(=O)N1C2=CC=C(Cl)C=C2C(O)CCC1 GYHCTFXIZSNGJT-UHFFFAOYSA-N 0.000 description 1
- 229960001256 tolvaptan Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 229960005461 torasemide Drugs 0.000 description 1
- 229960002051 trandolapril Drugs 0.000 description 1
- 229960005294 triamcinolone Drugs 0.000 description 1
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229950002929 trinitrophenol Drugs 0.000 description 1
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- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
- 229960001130 urapidil Drugs 0.000 description 1
- 239000000777 urocortin Substances 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Diabetes (AREA)
- Obesity (AREA)
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- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Child & Adolescent Psychology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200300569 | 2003-04-11 | ||
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006522749A true JP2006522749A (ja) | 2006-10-05 |
| JP2006522749A5 JP2006522749A5 (https=) | 2007-05-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP1615697A2 (https=) |
| JP (1) | JP2006522749A (https=) |
| WO (1) | WO2004089471A2 (https=) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2006522744A (ja) * | 2003-04-11 | 2006-10-05 | ノボ ノルディスク アクティーゼルスカブ | グルココルチコイド受容体アゴニスト療法に伴う副作用を最小化するための、１１β−ヒドロキシステロイドデヒドロゲナーゼ１型阻害剤およびグルココルチコイド受容体アゴニストを使用する併用療法 |
| JP2006522750A (ja) * | 2003-04-11 | 2006-10-05 | ノボ ノルディスク アクティーゼルスカブ | 代謝性症候群ならびに関連の疾患および障害を治療するために、１１β−ヒドロキシステロイドデヒドロゲナーゼ１型阻害剤および抗高血圧剤を使用する併用療法 |
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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 |
| US12336982B2 (en) | 2018-11-21 | 2025-06-24 | Rodeo Therapeutics Corporation | Compositions and methods of modulating short-chain dehydrogenase activity |
| JP2025102891A (ja) * | 2017-02-06 | 2025-07-08 | ケース ウエスタン リザーブ ユニバーシティ | 短鎖デヒドロゲナーゼ活性を調節する組成物と方法 |
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| US8415354B2 (en) | 2004-04-29 | 2013-04-09 | Abbott Laboratories | Methods of use of inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| US20100222316A1 (en) | 2004-04-29 | 2010-09-02 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| US7880001B2 (en) | 2004-04-29 | 2011-02-01 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase Type 1 enzyme |
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| JP5133702B2 (ja) | 2005-01-05 | 2013-01-30 | アボット・ラボラトリーズ | １１−β−ヒドロキシステロイドデヒドロゲナーゼ１型酵素の阻害薬 |
| DK1928840T3 (da) | 2005-04-05 | 2011-09-12 | Hoffmann La Roche | 1H-pyrazol-4-carboxamider, deres fremstilling og deres anvendelse som 11-beta-hydroxysteroid-dehydrogenaseinhibitorer |
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| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| JP5736098B2 (ja) | 2007-08-21 | 2015-06-17 | アッヴィ・インコーポレイテッド | 中枢神経系障害を治療するための医薬組成物 |
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| WO2018215389A1 (en) | 2017-05-22 | 2018-11-29 | F. Hoffmann-La Roche Ag | Therapeutic compounds and compositions, and methods of use thereof |
| AU2019370200B2 (en) | 2018-10-30 | 2024-12-19 | Kronos Bio, Inc. | Compounds, compositions, and methods for modulating CDK9 activity |
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| CA3220630A1 (en) * | 2021-06-02 | 2022-12-08 | Otsuka Pharmaceutical Co., Ltd. | Pyrazolo[1,5-a]pyrimidine compound for the treatment of dermal disorders |
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- 2004-04-06 JP JP2006504356A patent/JP2006522749A/ja active Pending
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006522744A (ja) * | 2003-04-11 | 2006-10-05 | ノボ ノルディスク アクティーゼルスカブ | グルココルチコイド受容体アゴニスト療法に伴う副作用を最小化するための、１１β−ヒドロキシステロイドデヒドロゲナーゼ１型阻害剤およびグルココルチコイド受容体アゴニストを使用する併用療法 |
| JP2006522750A (ja) * | 2003-04-11 | 2006-10-05 | ノボ ノルディスク アクティーゼルスカブ | 代謝性症候群ならびに関連の疾患および障害を治療するために、１１β−ヒドロキシステロイドデヒドロゲナーゼ１型阻害剤および抗高血圧剤を使用する併用療法 |
| JP2015511615A (ja) * | 2012-03-29 | 2015-04-20 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規なピラゾロピリミジン |
| JP2025102891A (ja) * | 2017-02-06 | 2025-07-08 | ケース ウエスタン リザーブ ユニバーシティ | 短鎖デヒドロゲナーゼ活性を調節する組成物と方法 |
| US12336982B2 (en) | 2018-11-21 | 2025-06-24 | Rodeo Therapeutics Corporation | Compositions and methods of modulating short-chain dehydrogenase activity |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1615697A2 (en) | 2006-01-18 |
| WO2004089471A3 (en) | 2004-12-23 |
| WO2004089471A2 (en) | 2004-10-21 |
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