JP2013536836A5 - - Google Patents
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- Publication number
- JP2013536836A5 JP2013536836A5 JP2013527016A JP2013527016A JP2013536836A5 JP 2013536836 A5 JP2013536836 A5 JP 2013536836A5 JP 2013527016 A JP2013527016 A JP 2013527016A JP 2013527016 A JP2013527016 A JP 2013527016A JP 2013536836 A5 JP2013536836 A5 JP 2013536836A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidin
- pyrazolo
- methanol
- pyrrolidin
- 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.)
- Granted
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- -1 chloro, bromo, iodo Chemical group 0.000 claims 74
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 18
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 12
- 125000001153 fluoro group Chemical group F* 0.000 claims 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 10
- 239000012453 solvate Substances 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 8
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 239000000651 prodrug Substances 0.000 claims 8
- 229940002612 prodrug Drugs 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000004434 sulfur atom Chemical group 0.000 claims 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 4
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 4
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 4
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 208000008589 Obesity Diseases 0.000 claims 3
- MNBZDFHKNFYYDQ-UHFFFAOYSA-N [1-[7-(3,4-difluorophenyl)-2-methyl-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(F)C(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 MNBZDFHKNFYYDQ-UHFFFAOYSA-N 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 229930003827 cannabinoid Natural products 0.000 claims 3
- 239000003557 cannabinoid Substances 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
- 102000005962 receptors Human genes 0.000 claims 3
- 108020003175 receptors Proteins 0.000 claims 3
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 206010028813 Nausea Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- PDWFQLZCPBWUDK-UHFFFAOYSA-N [1-[2-(ethoxymethyl)-7-(4-fluorophenyl)-3-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCOCC1=NN2C(C=3C=CC(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(OC)C=C1 PDWFQLZCPBWUDK-UHFFFAOYSA-N 0.000 claims 2
- DBPKZLMXSZPTQD-UHFFFAOYSA-N [1-[3-(3,4-difluorophenyl)-2-methyl-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(F)C(F)=C1 DBPKZLMXSZPTQD-UHFFFAOYSA-N 0.000 claims 2
- GHZGXRHAQHAHFX-UHFFFAOYSA-N [1-[3-(4-chlorophenyl)-2-(ethoxymethyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCOCC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(Cl)C=C1 GHZGXRHAQHAHFX-UHFFFAOYSA-N 0.000 claims 2
- FEZJTDHXIMXIEK-UHFFFAOYSA-N [1-[3-(4-ethylphenyl)-2-methyl-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(CC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=C(C=CC=3)C(F)(F)F)N2N=C1C FEZJTDHXIMXIEK-UHFFFAOYSA-N 0.000 claims 2
- RVJXLBOEJKWYEQ-UHFFFAOYSA-N [1-[7-(3,5-difluorophenyl)-3-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=C(F)C=C(F)C=3)N2N=C1C RVJXLBOEJKWYEQ-UHFFFAOYSA-N 0.000 claims 2
- XXXJKSSBWDXGAW-UHFFFAOYSA-N [1-[7-(3-chlorophenyl)-2-methyl-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(Cl)C=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 XXXJKSSBWDXGAW-UHFFFAOYSA-N 0.000 claims 2
- KYVWPIKFZMTKBR-UHFFFAOYSA-N [1-[7-(4-fluorophenyl)-2-methyl-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=CC(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 KYVWPIKFZMTKBR-UHFFFAOYSA-N 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
- 230000008693 nausea Effects 0.000 claims 2
- MQCKPPMNHICBFU-UHFFFAOYSA-N 1-[4-[7-(4-fluorophenyl)-5-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-3-yl]phenyl]ethanol Chemical compound C1=CC(C(O)C)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=CC(F)=CC=3)N2N=C1C MQCKPPMNHICBFU-UHFFFAOYSA-N 0.000 claims 1
- JIYUJADIQYTFSY-UHFFFAOYSA-N 2-[[2-(ethoxymethyl)-3-(4-methylphenyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino]ethanol Chemical compound CCOCC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N(C)CCO)=NC2=C1C1=CC=C(C)C=C1 JIYUJADIQYTFSY-UHFFFAOYSA-N 0.000 claims 1
- BKZQTSSTWGKBBO-UHFFFAOYSA-N 2-[[2-(ethoxymethyl)-7-(3-fluorophenyl)-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino]ethanol Chemical compound CCOCC1=NN2C(C=3C=C(F)C=CC=3)=CC(N(C)CCO)=NC2=C1C1=CC=C(C)C=C1 BKZQTSSTWGKBBO-UHFFFAOYSA-N 0.000 claims 1
- SDQCUDVDCZVTPV-UHFFFAOYSA-N 2-[[2-(methoxymethyl)-3-(4-methoxyphenyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino]ethanol Chemical compound COCC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N(C)CCO)=NC2=C1C1=CC=C(OC)C=C1 SDQCUDVDCZVTPV-UHFFFAOYSA-N 0.000 claims 1
- ZCSXCUHQORHJJW-UHFFFAOYSA-N 2-[[2-butyl-3-(4-methylphenyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino]ethanol Chemical compound CCCCC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N(C)CCO)=NC2=C1C1=CC=C(C)C=C1 ZCSXCUHQORHJJW-UHFFFAOYSA-N 0.000 claims 1
- DPARZUNIYWBNKC-UHFFFAOYSA-N 2-[[3-(1,3-benzodioxol-5-yl)-7-(3-chlorophenyl)-2-(ethoxymethyl)pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino]ethanol Chemical compound C=1C(N(C)CCO)=NC2=C(C=3C=C4OCOC4=CC=3)C(COCC)=NN2C=1C1=CC=CC(Cl)=C1 DPARZUNIYWBNKC-UHFFFAOYSA-N 0.000 claims 1
- HYBHLUDFJVRRSM-UHFFFAOYSA-N 2-[[3-(4-chlorophenyl)-2-(ethoxymethyl)-7-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino]ethanol Chemical compound CCOCC1=NN2C(C=3C=C(F)C=CC=3)=CC(N(C)CCO)=NC2=C1C1=CC=C(Cl)C=C1 HYBHLUDFJVRRSM-UHFFFAOYSA-N 0.000 claims 1
- RINGSIDZBGZJIW-UHFFFAOYSA-N 2-[[3-(4-chlorophenyl)-2-(ethoxymethyl)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-ethylamino]ethanol Chemical compound CCOCC1=NN2C(C=3C=CC(F)=CC=3)=CC(N(CC)CCO)=NC2=C1C1=CC=C(Cl)C=C1 RINGSIDZBGZJIW-UHFFFAOYSA-N 0.000 claims 1
- BOMBEXZTLUWWNS-UHFFFAOYSA-N 2-[[3-(4-chlorophenyl)-2-(ethoxymethyl)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino]ethanol Chemical compound CCOCC1=NN2C(C=3C=CC(F)=CC=3)=CC(N(C)CCO)=NC2=C1C1=CC=C(Cl)C=C1 BOMBEXZTLUWWNS-UHFFFAOYSA-N 0.000 claims 1
- WPDAUSFQRGSCGK-UHFFFAOYSA-N 2-[[3-(4-chlorophenyl)-2-(ethoxymethyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino]ethanol Chemical compound CCOCC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N(C)CCO)=NC2=C1C1=CC=C(Cl)C=C1 WPDAUSFQRGSCGK-UHFFFAOYSA-N 0.000 claims 1
- COHPMAMRVDFHRF-UHFFFAOYSA-N 2-[[3-(4-chlorophenyl)-2-(methoxymethyl)-7-(3-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino]ethanol Chemical compound COCC1=NN2C(C=3C=C(C)C=CC=3)=CC(N(C)CCO)=NC2=C1C1=CC=C(Cl)C=C1 COHPMAMRVDFHRF-UHFFFAOYSA-N 0.000 claims 1
- QPJDHYLHSQFJRA-UHFFFAOYSA-N 2-[[3-(4-chlorophenyl)-2-(methoxymethyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino]ethanol Chemical compound COCC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N(C)CCO)=NC2=C1C1=CC=C(Cl)C=C1 QPJDHYLHSQFJRA-UHFFFAOYSA-N 0.000 claims 1
- SHBFIJGSXZOUMR-UHFFFAOYSA-N 2-[[3-(4-chlorophenyl)-7-(3-fluorophenyl)-2-(methoxymethyl)pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino]ethanol Chemical compound COCC1=NN2C(C=3C=C(F)C=CC=3)=CC(N(C)CCO)=NC2=C1C1=CC=C(Cl)C=C1 SHBFIJGSXZOUMR-UHFFFAOYSA-N 0.000 claims 1
- MWMCQSKPIRCHEZ-UHFFFAOYSA-N 2-[[3-(4-chlorophenyl)-7-(4-fluorophenyl)-2-(methoxymethyl)pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino]ethanol Chemical compound COCC1=NN2C(C=3C=CC(F)=CC=3)=CC(N(C)CCO)=NC2=C1C1=CC=C(Cl)C=C1 MWMCQSKPIRCHEZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims 1
- 208000006029 Cardiomegaly Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000030990 Impulse-control disease Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010029216 Nervousness Diseases 0.000 claims 1
- 206010029897 Obsessive thoughts Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 208000007107 Stomach Ulcer Diseases 0.000 claims 1
- PQSRRWWIULESTR-QFIPXVFZSA-N [(2s)-1-[2-(ethoxymethyl)-3-(4-methoxyphenyl)-7-(3-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCOCC1=NN2C(C=3C=C(C)C=CC=3)=CC(N3[C@@H](CCC3)CO)=NC2=C1C1=CC=C(OC)C=C1 PQSRRWWIULESTR-QFIPXVFZSA-N 0.000 claims 1
- AMBRSLTZVMQNFO-DEOSSOPVSA-N [(2s)-1-[2-butyl-7-(3-methylphenyl)-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCCCC1=NN2C(C=3C=C(C)C=CC=3)=CC(N3[C@@H](CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 AMBRSLTZVMQNFO-DEOSSOPVSA-N 0.000 claims 1
- OFTBBBFTOGYCHR-NRFANRHFSA-N [(2s)-1-[3-(4-chlorophenyl)-2-(methoxymethyl)-7-(3-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound COCC1=NN2C(C=3C=C(C)C=CC=3)=CC(N3[C@@H](CCC3)CO)=NC2=C1C1=CC=C(Cl)C=C1 OFTBBBFTOGYCHR-NRFANRHFSA-N 0.000 claims 1
- XCAKXUYUVJELLT-FQEVSTJZSA-N [(2s)-1-[3-(4-chlorophenyl)-2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=CC=CC=3)=CC(N3[C@@H](CCC3)CO)=NC2=C1C1=CC=C(Cl)C=C1 XCAKXUYUVJELLT-FQEVSTJZSA-N 0.000 claims 1
- USQDDAWNOFWURT-FQEVSTJZSA-N [(2s)-1-[3-(4-chlorophenyl)-7-(3-fluorophenyl)-2-(methoxymethyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound COCC1=NN2C(C=3C=C(F)C=CC=3)=CC(N3[C@@H](CCC3)CO)=NC2=C1C1=CC=C(Cl)C=C1 USQDDAWNOFWURT-FQEVSTJZSA-N 0.000 claims 1
- PAMBMSKQBLTHIX-SFHVURJKSA-N [(2s)-1-[7-(2-fluorophenyl)-2-(methoxymethyl)-3-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound COCC1=NN2C(C=3C(=CC=CC=3)F)=CC(N3[C@@H](CCC3)CO)=NC2=C1C1=CC=C(OC)C=C1 PAMBMSKQBLTHIX-SFHVURJKSA-N 0.000 claims 1
- WQVYUOZMNAVGJI-IBGZPJMESA-N [(2s)-1-[7-(3,4-difluorophenyl)-3-(4-ethoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(OCC)=CC=C1C1=C2N=C(N3[C@@H](CCC3)CO)C=C(C=3C=C(F)C(F)=CC=3)N2N=C1C WQVYUOZMNAVGJI-IBGZPJMESA-N 0.000 claims 1
- REVSWHHKHVVLJL-FQEVSTJZSA-N [(2s)-1-[7-(3-chlorophenyl)-2-(methoxymethyl)-3-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound COCC1=NN2C(C=3C=C(Cl)C=CC=3)=CC(N3[C@@H](CCC3)CO)=NC2=C1C1=CC=C(OC)C=C1 REVSWHHKHVVLJL-FQEVSTJZSA-N 0.000 claims 1
- RDHZBHURQBWOJP-FQEVSTJZSA-N [(2s)-1-[7-(4-chlorophenyl)-2-(methoxymethyl)-3-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound COCC1=NN2C(C=3C=CC(Cl)=CC=3)=CC(N3[C@@H](CCC3)CO)=NC2=C1C1=CC=C(OC)C=C1 RDHZBHURQBWOJP-FQEVSTJZSA-N 0.000 claims 1
- ZRZXKBZLPCVIJL-UHFFFAOYSA-N [1-[2-(difluoromethyl)-3-(4-methoxyphenyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=C(C=CC=3)C(F)(F)F)N2N=C1C(F)F ZRZXKBZLPCVIJL-UHFFFAOYSA-N 0.000 claims 1
- PSPPWWHHSJXGBI-UHFFFAOYSA-N [1-[2-(ethoxymethyl)-3-(4-methoxyphenyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCOCC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(OC)C=C1 PSPPWWHHSJXGBI-UHFFFAOYSA-N 0.000 claims 1
- RKKIVRPFYVUABL-UHFFFAOYSA-N [1-[2-(ethoxymethyl)-3-(4-methylphenyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCOCC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 RKKIVRPFYVUABL-UHFFFAOYSA-N 0.000 claims 1
- BPRZJMAZQXNZNQ-UHFFFAOYSA-N [1-[2-(ethoxymethyl)-7-(3-fluorophenyl)-3-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCOCC1=NN2C(C=3C=C(F)C=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(OC)C=C1 BPRZJMAZQXNZNQ-UHFFFAOYSA-N 0.000 claims 1
- IPDDARVGSUZKEM-UHFFFAOYSA-N [1-[2-(ethoxymethyl)-7-(3-fluorophenyl)-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCOCC1=NN2C(C=3C=C(F)C=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 IPDDARVGSUZKEM-UHFFFAOYSA-N 0.000 claims 1
- YXUBOGXASHCQEB-UHFFFAOYSA-N [1-[2-(ethoxymethyl)-7-(3-methoxyphenyl)-3-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCOCC1=NN2C(C=3C=C(OC)C=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(OC)C=C1 YXUBOGXASHCQEB-UHFFFAOYSA-N 0.000 claims 1
- WSOZTHHHUOHXIS-UHFFFAOYSA-N [1-[2-(ethoxymethyl)-7-(3-methoxyphenyl)-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCOCC1=NN2C(C=3C=C(OC)C=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 WSOZTHHHUOHXIS-UHFFFAOYSA-N 0.000 claims 1
- UNHNUVQTVXMIPR-UHFFFAOYSA-N [1-[2-(ethoxymethyl)-7-(3-methylphenyl)-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCOCC1=NN2C(C=3C=C(C)C=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 UNHNUVQTVXMIPR-UHFFFAOYSA-N 0.000 claims 1
- RXUAACSWZAAWND-UHFFFAOYSA-N [1-[2-(methoxymethyl)-3-(4-methoxyphenyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound COCC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(OC)C=C1 RXUAACSWZAAWND-UHFFFAOYSA-N 0.000 claims 1
- SYYFFWHEMCUVGM-UHFFFAOYSA-N [1-[2-butyl-3-(4-methylphenyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCCCC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 SYYFFWHEMCUVGM-UHFFFAOYSA-N 0.000 claims 1
- LRVLXTUPXKYCLT-UHFFFAOYSA-N [1-[2-cyclopropyl-3-(2,4-dichlorophenyl)-7-(2-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound OCC1CCCN1C1=NC2=C(C=3C(=CC(Cl)=CC=3)Cl)C(C3CC3)=NN2C(C=2C(=CC=CC=2)F)=C1 LRVLXTUPXKYCLT-UHFFFAOYSA-N 0.000 claims 1
- CIWXDUKWFDXRNA-UHFFFAOYSA-N [1-[2-cyclopropyl-3-(2,4-dichlorophenyl)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound OCC1CCCN1C1=NC2=C(C=3C(=CC(Cl)=CC=3)Cl)C(C3CC3)=NN2C(C=2C=CC(F)=CC=2)=C1 CIWXDUKWFDXRNA-UHFFFAOYSA-N 0.000 claims 1
- SDIBTTIECRVKKD-UHFFFAOYSA-N [1-[2-ethyl-7-(3-fluorophenyl)-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCC1=NN2C(C=3C=C(F)C=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 SDIBTTIECRVKKD-UHFFFAOYSA-N 0.000 claims 1
- LKBXHHHRKZBXHH-UHFFFAOYSA-N [1-[2-ethyl-7-(4-fluorophenyl)-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCC1=NN2C(C=3C=CC(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 LKBXHHHRKZBXHH-UHFFFAOYSA-N 0.000 claims 1
- BOZHZAVQZPJJRH-UHFFFAOYSA-N [1-[2-methyl-3,7-bis(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=CC(C)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 BOZHZAVQZPJJRH-UHFFFAOYSA-N 0.000 claims 1
- HHKDQQSTMSVVOJ-UHFFFAOYSA-N [1-[2-methyl-3-(4-methylphenyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 HHKDQQSTMSVVOJ-UHFFFAOYSA-N 0.000 claims 1
- SXDQAUFGEZADKG-UHFFFAOYSA-N [1-[2-methyl-3-(4-methylsulfanylphenyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(SC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=C(C=CC=3)C(F)(F)F)N2N=C1C SXDQAUFGEZADKG-UHFFFAOYSA-N 0.000 claims 1
- VVNFYCWIWWGSSU-UHFFFAOYSA-N [1-[2-methyl-7-(3-methylphenyl)-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(C)C=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 VVNFYCWIWWGSSU-UHFFFAOYSA-N 0.000 claims 1
- BALJINHVRMQDHT-UHFFFAOYSA-N [1-[2-methyl-7-[3-(trifluoromethyl)phenyl]-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C(F)(F)F)C=C1 BALJINHVRMQDHT-UHFFFAOYSA-N 0.000 claims 1
- JVRCTBRTYRKSLR-UHFFFAOYSA-N [1-[3,7-bis(4-chlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=CC(Cl)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(Cl)C=C1 JVRCTBRTYRKSLR-UHFFFAOYSA-N 0.000 claims 1
- WZRWNNOJFSCIAV-UHFFFAOYSA-N [1-[3-(1,3-benzodioxol-5-yl)-2-(ethoxymethyl)-7-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound N=1C2=C(C=3C=C4OCOC4=CC=3)C(COCC)=NN2C(C=2C=C(F)C=CC=2)=CC=1N1CCCC1CO WZRWNNOJFSCIAV-UHFFFAOYSA-N 0.000 claims 1
- FOOJGHKHVVZNAN-UHFFFAOYSA-N [1-[3-(1,3-benzodioxol-5-yl)-2-(ethoxymethyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound N=1C2=C(C=3C=C4OCOC4=CC=3)C(COCC)=NN2C(C=2C=C(C=CC=2)C(F)(F)F)=CC=1N1CCCC1CO FOOJGHKHVVZNAN-UHFFFAOYSA-N 0.000 claims 1
- WFIHVKJBDLDLCD-UHFFFAOYSA-N [1-[3-(1,3-benzodioxol-5-yl)-2-(methoxymethyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound N=1C2=C(C=3C=C4OCOC4=CC=3)C(COC)=NN2C(C=2C=C(C=CC=2)C(F)(F)F)=CC=1N1CCCC1CO WFIHVKJBDLDLCD-UHFFFAOYSA-N 0.000 claims 1
- QZVNDDFLZAMTRR-UHFFFAOYSA-N [1-[3-(1,3-benzodioxol-5-yl)-2-methyl-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound N=1C2=C(C=3C=C4OCOC4=CC=3)C(C)=NN2C(C=2C=C(C=CC=2)C(F)(F)F)=CC=1N1CCCC1CO QZVNDDFLZAMTRR-UHFFFAOYSA-N 0.000 claims 1
- RMIZKIRDSPSMEX-UHFFFAOYSA-N [1-[3-(1,3-benzodioxol-5-yl)-2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound N=1C2=C(C=3C=C4OCOC4=CC=3)C(C)=NN2C(C=2C=CC=CC=2)=CC=1N1CCCC1CO RMIZKIRDSPSMEX-UHFFFAOYSA-N 0.000 claims 1
- XKCNDVJHBHMMLF-UHFFFAOYSA-N [1-[3-(1,3-benzodioxol-5-yl)-7-(3-chlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound N=1C2=C(C=3C=C4OCOC4=CC=3)C(C)=NN2C(C=2C=C(Cl)C=CC=2)=CC=1N1CCCC1CO XKCNDVJHBHMMLF-UHFFFAOYSA-N 0.000 claims 1
- TZMNUWQGROBECC-UHFFFAOYSA-N [1-[3-(1,3-benzodioxol-5-yl)-7-(3-fluorophenyl)-2-(methoxymethyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound N=1C2=C(C=3C=C4OCOC4=CC=3)C(COC)=NN2C(C=2C=C(F)C=CC=2)=CC=1N1CCCC1CO TZMNUWQGROBECC-UHFFFAOYSA-N 0.000 claims 1
- ZCXJVVVBVFXYOS-UHFFFAOYSA-N [1-[3-(1,3-benzodioxol-5-yl)-7-(4-fluorophenyl)-2-(methoxymethyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound N=1C2=C(C=3C=C4OCOC4=CC=3)C(COC)=NN2C(C=2C=CC(F)=CC=2)=CC=1N1CCCC1CO ZCXJVVVBVFXYOS-UHFFFAOYSA-N 0.000 claims 1
- KWJHHSUBXBBWKA-UHFFFAOYSA-N [1-[3-(2,4-difluorophenyl)-2-methyl-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(F)C=C1F KWJHHSUBXBBWKA-UHFFFAOYSA-N 0.000 claims 1
- ORDOZYZWWQMBMD-UHFFFAOYSA-N [1-[3-(2,4-difluorophenyl)-7-(3-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound COC1=CC=CC(C=2N3N=C(C)C(=C3N=C(C=2)N2C(CCC2)CO)C=2C(=CC(F)=CC=2)F)=C1 ORDOZYZWWQMBMD-UHFFFAOYSA-N 0.000 claims 1
- ULGLPZKRZUIXRD-UHFFFAOYSA-N [1-[3-(2,4-difluorophenyl)-7-(4-fluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=CC(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(F)C=C1F ULGLPZKRZUIXRD-UHFFFAOYSA-N 0.000 claims 1
- OQOQKOZTDNAOEL-UHFFFAOYSA-N [1-[3-(3-fluoro-4-methylphenyl)-2-methyl-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C(F)=C1 OQOQKOZTDNAOEL-UHFFFAOYSA-N 0.000 claims 1
- CGWUCDACJSLQEH-UHFFFAOYSA-N [1-[3-(3-fluoro-4-methylphenyl)-7-(3-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound COC1=CC=CC(C=2N3N=C(C)C(=C3N=C(C=2)N2C(CCC2)CO)C=2C=C(F)C(C)=CC=2)=C1 CGWUCDACJSLQEH-UHFFFAOYSA-N 0.000 claims 1
- BQOJJNCXNLNGCS-UHFFFAOYSA-N [1-[3-(3-fluoro-4-methylphenyl)-7-(4-fluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=CC(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C(F)=C1 BQOJJNCXNLNGCS-UHFFFAOYSA-N 0.000 claims 1
- REKRHVDQASGROV-UHFFFAOYSA-N [1-[3-(4-butoxyphenyl)-7-(4-fluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(OCCCC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=CC(F)=CC=3)N2N=C1C REKRHVDQASGROV-UHFFFAOYSA-N 0.000 claims 1
- RIYGTPQEANCNFU-UHFFFAOYSA-N [1-[3-(4-chlorophenyl)-2-(ethoxymethyl)-7-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCOCC1=NN2C(C=3C=C(F)C=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(Cl)C=C1 RIYGTPQEANCNFU-UHFFFAOYSA-N 0.000 claims 1
- BSNSLUBVKWBZEG-UHFFFAOYSA-N [1-[3-(4-chlorophenyl)-2-(ethoxymethyl)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCOCC1=NN2C(C=3C=CC(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(Cl)C=C1 BSNSLUBVKWBZEG-UHFFFAOYSA-N 0.000 claims 1
- DELUUFVZGYLITQ-UHFFFAOYSA-N [1-[3-(4-chlorophenyl)-2-methyl-7-(3-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(C)C=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(Cl)C=C1 DELUUFVZGYLITQ-UHFFFAOYSA-N 0.000 claims 1
- XGSYFEWLZQMSAW-UHFFFAOYSA-N [1-[3-(4-chlorophenyl)-7-(2,4-difluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C(=CC(F)=CC=3)F)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(Cl)C=C1 XGSYFEWLZQMSAW-UHFFFAOYSA-N 0.000 claims 1
- ICGCWOHOAVCPHO-UHFFFAOYSA-N [1-[3-(4-chlorophenyl)-7-(3,4-difluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(F)C(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(Cl)C=C1 ICGCWOHOAVCPHO-UHFFFAOYSA-N 0.000 claims 1
- IPQWOXIYXGLGJD-UHFFFAOYSA-N [1-[3-(4-chlorophenyl)-7-(3-ethylphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCC1=CC=CC(C=2N3N=C(C)C(=C3N=C(C=2)N2C(CCC2)CO)C=2C=CC(Cl)=CC=2)=C1 IPQWOXIYXGLGJD-UHFFFAOYSA-N 0.000 claims 1
- USQDDAWNOFWURT-UHFFFAOYSA-N [1-[3-(4-chlorophenyl)-7-(3-fluorophenyl)-2-(methoxymethyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound COCC1=NN2C(C=3C=C(F)C=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(Cl)C=C1 USQDDAWNOFWURT-UHFFFAOYSA-N 0.000 claims 1
- NWSFNOPXTKXJAQ-UHFFFAOYSA-N [1-[3-(4-chlorophenyl)-7-(3-fluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(F)C=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(Cl)C=C1 NWSFNOPXTKXJAQ-UHFFFAOYSA-N 0.000 claims 1
- JJFUUCJQVZOGPS-UHFFFAOYSA-N [1-[3-(4-chlorophenyl)-7-(4-fluorophenyl)-2-(methoxymethyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound COCC1=NN2C(C=3C=CC(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(Cl)C=C1 JJFUUCJQVZOGPS-UHFFFAOYSA-N 0.000 claims 1
- OJLCZLSCFISIHT-UHFFFAOYSA-N [1-[3-(4-chlorophenyl)-7-(4-fluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=CC(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(Cl)C=C1 OJLCZLSCFISIHT-UHFFFAOYSA-N 0.000 claims 1
- ACMDBEAETALRSQ-UHFFFAOYSA-N [1-[3-(4-ethoxyphenyl)-2-methyl-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(OCC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=C(C=CC=3)C(F)(F)F)N2N=C1C ACMDBEAETALRSQ-UHFFFAOYSA-N 0.000 claims 1
- WNGSYZHLNZERAL-UHFFFAOYSA-N [1-[3-(4-ethoxyphenyl)-2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(OCC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=CC=CC=3)N2N=C1C WNGSYZHLNZERAL-UHFFFAOYSA-N 0.000 claims 1
- HLFUIBSYESKFDM-UHFFFAOYSA-N [1-[3-(4-ethoxyphenyl)-7-(4-fluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(OCC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=CC(F)=CC=3)N2N=C1C HLFUIBSYESKFDM-UHFFFAOYSA-N 0.000 claims 1
- FKAHZVZJIXCQTB-UHFFFAOYSA-N [1-[3-(4-ethoxyphenyl)-7-[3-(fluoromethyl)phenyl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(OCC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=C(CF)C=CC=3)N2N=C1C FKAHZVZJIXCQTB-UHFFFAOYSA-N 0.000 claims 1
- PBBYPQLICNGIDD-UHFFFAOYSA-N [1-[3-(4-ethylphenyl)-7-(4-fluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(CC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=CC(F)=CC=3)N2N=C1C PBBYPQLICNGIDD-UHFFFAOYSA-N 0.000 claims 1
- PBNLXRXNXIJKHM-UHFFFAOYSA-N [1-[3-(4-ethylsulfanylphenyl)-7-(4-fluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(SCC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=CC(F)=CC=3)N2N=C1C PBNLXRXNXIJKHM-UHFFFAOYSA-N 0.000 claims 1
- ZVNVZHKKHXHFSC-UHFFFAOYSA-N [1-[3-(4-fluoro-3-methylphenyl)-7-(4-fluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=CC(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(F)C(C)=C1 ZVNVZHKKHXHFSC-UHFFFAOYSA-N 0.000 claims 1
- WWRAQCBULMZIHS-UHFFFAOYSA-N [1-[3-(4-fluorophenyl)-2-methyl-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(F)C=C1 WWRAQCBULMZIHS-UHFFFAOYSA-N 0.000 claims 1
- LBFQIWUSXSACIL-UHFFFAOYSA-N [1-[3-(4-methoxyphenyl)-2-(trifluoromethyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=C(C=CC=3)C(F)(F)F)N2N=C1C(F)(F)F LBFQIWUSXSACIL-UHFFFAOYSA-N 0.000 claims 1
- CQLHWOILQLKTBD-UHFFFAOYSA-N [1-[3-(4-methoxyphenyl)-2-methyl-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=C(C=CC=3)C(F)(F)F)N2N=C1C CQLHWOILQLKTBD-UHFFFAOYSA-N 0.000 claims 1
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- ZRVYFVFRZURSGE-UHFFFAOYSA-N [1-[3-[4-(difluoromethyl)phenyl]-2-methyl-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C(F)F)C=C1 ZRVYFVFRZURSGE-UHFFFAOYSA-N 0.000 claims 1
- ZCUFLVKCUURWMO-UHFFFAOYSA-N [1-[3-[4-(difluoromethyl)phenyl]-7-(3-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound COC1=CC=CC(C=2N3N=C(C)C(=C3N=C(C=2)N2C(CCC2)CO)C=2C=CC(=CC=2)C(F)F)=C1 ZCUFLVKCUURWMO-UHFFFAOYSA-N 0.000 claims 1
- BRONGZWCDDTNEK-UHFFFAOYSA-N [1-[3-[4-(difluoromethyl)phenyl]-7-(4-fluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=CC(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C(F)F)C=C1 BRONGZWCDDTNEK-UHFFFAOYSA-N 0.000 claims 1
- IDQNCAISMAGUJO-UHFFFAOYSA-N [1-[7-(2-fluorophenyl)-2-methyl-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C(=CC=CC=3)F)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 IDQNCAISMAGUJO-UHFFFAOYSA-N 0.000 claims 1
- YQHCYPCGVUYMJW-UHFFFAOYSA-N [1-[7-(3,4-difluorophenyl)-3-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=C(F)C(F)=CC=3)N2N=C1C YQHCYPCGVUYMJW-UHFFFAOYSA-N 0.000 claims 1
- JNIZOHGDGNPVDX-UHFFFAOYSA-N [1-[7-(3-chloro-4-fluorophenyl)-2-methyl-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(Cl)C(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 JNIZOHGDGNPVDX-UHFFFAOYSA-N 0.000 claims 1
- MLHPVDKXXPVHCC-UHFFFAOYSA-N [1-[7-(3-chloro-4-fluorophenyl)-3-(4-fluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(Cl)C(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(F)C=C1 MLHPVDKXXPVHCC-UHFFFAOYSA-N 0.000 claims 1
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- CKRAFILOIJZYDG-UHFFFAOYSA-N [1-[7-(3-chlorophenyl)-2-ethyl-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCC1=NN2C(C=3C=C(Cl)C=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 CKRAFILOIJZYDG-UHFFFAOYSA-N 0.000 claims 1
- OGYCUCUFABMUHE-UHFFFAOYSA-N [1-[7-(3-chlorophenyl)-3-(4-chlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(Cl)C=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(Cl)C=C1 OGYCUCUFABMUHE-UHFFFAOYSA-N 0.000 claims 1
- DKAGEAKFMHUXMX-UHFFFAOYSA-N [1-[7-(3-chlorophenyl)-3-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=C(Cl)C=CC=3)N2N=C1C DKAGEAKFMHUXMX-UHFFFAOYSA-N 0.000 claims 1
- UPJKBPHJPYYQRW-UHFFFAOYSA-N [1-[7-(3-ethylphenyl)-2-methyl-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CCC1=CC=CC(C=2N3N=C(C)C(=C3N=C(C=2)N2C(CCC2)CO)C=2C=CC(C)=CC=2)=C1 UPJKBPHJPYYQRW-UHFFFAOYSA-N 0.000 claims 1
- HKCNSWFVWXTXNQ-UHFFFAOYSA-N [1-[7-(3-fluorophenyl)-2-methyl-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=C(F)C=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 HKCNSWFVWXTXNQ-UHFFFAOYSA-N 0.000 claims 1
- ICHBGHZXDBZUHG-UHFFFAOYSA-N [1-[7-(3-methoxyphenyl)-2-methyl-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound COC1=CC=CC(C=2N3N=C(C)C(=C3N=C(C=2)N2C(CCC2)CO)C=2C=CC(C)=CC=2)=C1 ICHBGHZXDBZUHG-UHFFFAOYSA-N 0.000 claims 1
- IURRCNZULHYFLF-UHFFFAOYSA-N [1-[7-(3-methoxyphenyl)-2-methyl-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound COC1=CC=CC(C=2N3N=C(C)C(=C3N=C(C=2)N2C(CCC2)CO)C=2C=CC(=CC=2)C(F)(F)F)=C1 IURRCNZULHYFLF-UHFFFAOYSA-N 0.000 claims 1
- MPGHFKAZHTYNHT-UHFFFAOYSA-N [1-[7-(4-chlorophenyl)-2-methyl-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=CC(Cl)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C)C=C1 MPGHFKAZHTYNHT-UHFFFAOYSA-N 0.000 claims 1
- YRTXRKQJCPOTGY-UHFFFAOYSA-N [1-[7-(4-chlorophenyl)-3-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=CC(Cl)=CC=3)N2N=C1C YRTXRKQJCPOTGY-UHFFFAOYSA-N 0.000 claims 1
- ILAADFIJHUHTJH-UHFFFAOYSA-N [1-[7-(4-fluorophenyl)-2-(methoxymethyl)-3-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound COCC1=NN2C(C=3C=CC(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(OC)C=C1 ILAADFIJHUHTJH-UHFFFAOYSA-N 0.000 claims 1
- NIPQDVWSFMBANW-UHFFFAOYSA-N [1-[7-(4-fluorophenyl)-2-methyl-3-(4-methylsulfanylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(SC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=CC(F)=CC=3)N2N=C1C NIPQDVWSFMBANW-UHFFFAOYSA-N 0.000 claims 1
- MQMYAOLRLRFQBX-UHFFFAOYSA-N [1-[7-(4-fluorophenyl)-2-methyl-3-(4-phenylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=CC(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C(C=C1)=CC=C1C1=CC=CC=C1 MQMYAOLRLRFQBX-UHFFFAOYSA-N 0.000 claims 1
- UIQFBTDZHYAYJT-UHFFFAOYSA-N [1-[7-(4-fluorophenyl)-2-methyl-3-(4-propoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(OCCC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=CC(F)=CC=3)N2N=C1C UIQFBTDZHYAYJT-UHFFFAOYSA-N 0.000 claims 1
- VJIBKFUMSQDSPU-UHFFFAOYSA-N [1-[7-(4-fluorophenyl)-2-methyl-3-[3-(trifluoromethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=CC(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=CC(OC(F)(F)F)=C1 VJIBKFUMSQDSPU-UHFFFAOYSA-N 0.000 claims 1
- NRKIKGIHJJMHEO-UHFFFAOYSA-N [1-[7-(4-fluorophenyl)-2-methyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=CC(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(OC(F)(F)F)C=C1 NRKIKGIHJJMHEO-UHFFFAOYSA-N 0.000 claims 1
- LCPPFXGFCOWAQJ-UHFFFAOYSA-N [1-[7-(4-fluorophenyl)-2-methyl-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound CC1=NN2C(C=3C=CC(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C1=CC=C(C(F)(F)F)C=C1 LCPPFXGFCOWAQJ-UHFFFAOYSA-N 0.000 claims 1
- RGMPNNYTAOQKBH-UHFFFAOYSA-N [1-[7-(4-fluorophenyl)-3-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1=C2N=C(N3C(CCC3)CO)C=C(C=3C=CC(F)=CC=3)N2N=C1C RGMPNNYTAOQKBH-UHFFFAOYSA-N 0.000 claims 1
- YNCNBSHJYCUBAI-UHFFFAOYSA-N [1-[7-(4-methoxyphenyl)-2-methyl-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1=CC(N2C(CCC2)CO)=NC2=C(C=3C=CC(C)=CC=3)C(C)=NN12 YNCNBSHJYCUBAI-UHFFFAOYSA-N 0.000 claims 1
- OAHPLYQYZYYWSW-UHFFFAOYSA-N [4-[7-(4-fluorophenyl)-5-[2-(hydroxymethyl)pyrrolidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-3-yl]phenyl] benzoate Chemical compound CC1=NN2C(C=3C=CC(F)=CC=3)=CC(N3C(CCC3)CO)=NC2=C1C(C=C1)=CC=C1OC(=O)C1=CC=CC=C1 OAHPLYQYZYYWSW-UHFFFAOYSA-N 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
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- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
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- 235000014632 disordered eating Nutrition 0.000 claims 1
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- 238000004519 manufacturing process Methods 0.000 claims 1
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- 238000000034 method Methods 0.000 claims 1
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- 230000002265 prevention Effects 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
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- 208000012201 sexual and gender identity disease Diseases 0.000 claims 1
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- 239000002904 solvent Substances 0.000 claims 1
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| PCT/KR2011/006474 WO2012030170A2 (ko) | 2010-08-31 | 2011-08-31 | 카나비노이드 1 수용체 저해제로 작용하는 신규 화합물 |
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| JP2013536836A JP2013536836A (ja) | 2013-09-26 |
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| JP2020531519A (ja) | 2017-08-21 | 2020-11-05 | ナビゲン，インコーポレーテッド | Ａｒｆ６阻害剤及び関連する方法 |
| CN109856394B (zh) * | 2019-04-16 | 2022-04-19 | 浙江诺迦生物科技有限公司 | 一种基于细胞多巴胺释放效应的大麻素类活性物质的检测方法及其检测试剂盒 |
| WO2020232350A1 (en) * | 2019-05-15 | 2020-11-19 | The Regents Of The University Of Colorado, A Body Corporate | Assays for synthetic cannabinoids |
| CN112007156A (zh) * | 2019-05-30 | 2020-12-01 | 复旦大学 | 大麻素受体药物在制备治疗心肌细胞坏死性凋亡药剂中的应用 |
| CN112755189A (zh) * | 2019-11-02 | 2021-05-07 | 复旦大学 | 1型大麻素受体拮抗剂在制备治疗心肌细胞焦亡药剂中的应用 |
| TWI907472B (zh) * | 2020-08-05 | 2025-12-11 | 匈牙利商羅特格登公司 | 具藥理活性之經雜環取代的吡唑并〔１，５－ａ〕嘧啶衍生物 |
| KR102912267B1 (ko) * | 2023-04-20 | 2026-01-15 | 한국화학연구원 | 신규한 헤테로고리 화합물 또는 이의 약학적으로 허용가능한 염 및 이를 유효성분으로 포함하는 바이러스성 질환의 예방 또는 치료용 약학적 조성물 |
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| GB0515026D0 (en) * | 2005-07-21 | 2005-08-31 | Novartis Ag | Organic compounds |
| TW201345908A (zh) * | 2006-07-05 | 2013-11-16 | Mitsubishi Tanabe Pharma Corp | 吡唑并〔１，５-ａ〕嘧啶化合物 |
| AR061793A1 (es) * | 2006-07-05 | 2008-09-24 | Mitsubishi Tanabe Pharma Corp | Compuesto de pirazolo[1,5-a] pirimidina y composicion farmaceutica |
| CN101671336B (zh) * | 2009-09-23 | 2013-11-13 | 辽宁利锋科技开发有限公司 | 芳杂环并嘧啶衍生物和类似物及其制备方法和用途 |
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- 2011-08-31 EP EP11822145.6A patent/EP2617723A4/en not_active Withdrawn
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- 2011-08-31 KR KR1020137005744A patent/KR101914161B1/ko not_active Expired - Fee Related
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