JP2013515692A - 新規抗ウイルス化合物 - Google Patents

Info

Publication number

JP2013515692A

JP2013515692A JP2012545282A JP2012545282A JP2013515692A JP 2013515692 A JP2013515692 A JP 2013515692A JP 2012545282 A JP2012545282 A JP 2012545282A JP 2012545282 A JP2012545282 A JP 2012545282A JP 2013515692 A JP2013515692 A JP 2013515692A

Authority

JP

Japan

Prior art keywords

heterocycle

alkyl

alkynyl

heteroalkyl

heteroalkenyl

Prior art date

2009-12-23

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.)

Ceased

Links

• Espacenet
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 350
• 230000000840 anti-viral effect Effects 0.000 title claims abstract description 14
• 238000000034 method Methods 0.000 claims abstract description 119
• 239000004480 active ingredient Substances 0.000 claims abstract description 40
• 239000003814 drug Substances 0.000 claims abstract description 31
• 208000036142 Viral infection Diseases 0.000 claims abstract description 27
• 230000009385 viral infection Effects 0.000 claims abstract description 27
• 241001465754 Metazoa Species 0.000 claims abstract description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
• 238000004519 manufacturing process Methods 0.000 claims abstract description 7
• -1 cycloalkynyl Chemical group 0.000 claims description 210
• 125000000217 alkyl group Chemical group 0.000 claims description 107
• 125000003118 aryl group Chemical group 0.000 claims description 107
• 125000003342 alkenyl group Chemical group 0.000 claims description 81
• 125000000304 alkynyl group Chemical group 0.000 claims description 75
• 125000000623 heterocyclic group Chemical group 0.000 claims description 75
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 72
• 229910052739 hydrogen Inorganic materials 0.000 claims description 50
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 45
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 41
• 125000005015 aryl alkynyl group Chemical group 0.000 claims description 41
• 229910052799 carbon Inorganic materials 0.000 claims description 40
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
• 229910052736 halogen Inorganic materials 0.000 claims description 34
• 150000002367 halogens Chemical class 0.000 claims description 34
• 150000003839 salts Chemical class 0.000 claims description 30
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 28
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
• 125000005842 heteroatom Chemical group 0.000 claims description 23
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 241000124008 Mammalia Species 0.000 claims description 15
• 125000001072 heteroaryl group Chemical group 0.000 claims description 15
• 230000002265 prevention Effects 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 8
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
• 150000002431 hydrogen Chemical class 0.000 claims description 6
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• 229920002554 vinyl polymer Polymers 0.000 claims description 5
• 208000015181 infectious disease Diseases 0.000 claims description 4
• 125000005670 ethenylalkyl group Chemical group 0.000 claims description 3
• 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 2
• 241000725303 Human immunodeficiency virus Species 0.000 abstract description 31
• 239000003795 chemical substances by application Substances 0.000 abstract description 13
• 208000031886 HIV Infections Diseases 0.000 abstract description 8
• 230000010076 replication Effects 0.000 abstract description 8
• 230000001225 therapeutic effect Effects 0.000 abstract description 6
• 230000002401 inhibitory effect Effects 0.000 abstract description 5
• 208000037357 HIV infectious disease Diseases 0.000 abstract description 3
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 abstract description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 411
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 272
• 239000000243 solution Substances 0.000 description 244
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 207
• 239000000543 intermediate Substances 0.000 description 155
• 238000002360 preparation method Methods 0.000 description 154
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 135
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 122
• 238000003818 flash chromatography Methods 0.000 description 118
• 239000000741 silica gel Substances 0.000 description 115
• 229910002027 silica gel Inorganic materials 0.000 description 115
• 238000000746 purification Methods 0.000 description 108
• 230000002829 reductive effect Effects 0.000 description 105
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 98
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 92
• 239000000203 mixture Substances 0.000 description 92
• 239000003921 oil Substances 0.000 description 77
• 235000019198 oils Nutrition 0.000 description 76
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 74
• 125000004432 carbon atom Chemical group C* 0.000 description 67
• 239000011541 reaction mixture Substances 0.000 description 65
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
• 239000007787 solid Substances 0.000 description 60
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 52
• 239000003039 volatile agent Substances 0.000 description 52
• 125000004429 atom Chemical group 0.000 description 51
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
• ZWNCJCPLPUBNCZ-UHFFFAOYSA-N 1,2-dimethoxyethane;hydrate Chemical compound O.COCCOC ZWNCJCPLPUBNCZ-UHFFFAOYSA-N 0.000 description 42
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 42
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 42
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
• 239000012267 brine Substances 0.000 description 40
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 40
• 150000001721 carbon Chemical group 0.000 description 36
• 239000012535 impurity Substances 0.000 description 35
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 35
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 35
• 238000009472 formulation Methods 0.000 description 33
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
• 239000012044 organic layer Substances 0.000 description 31
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
• 239000000047 product Substances 0.000 description 29
• JIYXANPMCJRVKB-UHFFFAOYSA-N methyl 2-(2-tert-butyl-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)pentanoate Chemical compound ClC1=C(C(C(=O)OC)CCC)C(C)=NC2=CC(C(C)(C)C)=NN21 JIYXANPMCJRVKB-UHFFFAOYSA-N 0.000 description 27
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 26
• 235000019341 magnesium sulphate Nutrition 0.000 description 26
• 239000010410 layer Substances 0.000 description 24
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 24
• 238000001816 cooling Methods 0.000 description 23
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 21
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
• 239000003112 inhibitor Substances 0.000 description 20
• 229930195733 hydrocarbon Natural products 0.000 description 18
• 125000001183 hydrocarbyl group Chemical group 0.000 description 18
• 150000003254 radicals Chemical class 0.000 description 18
• 239000002585 base Substances 0.000 description 17
• 235000019441 ethanol Nutrition 0.000 description 16
• 229910052760 oxygen Inorganic materials 0.000 description 16
• 229940002612 prodrug Drugs 0.000 description 16
• 239000000651 prodrug Substances 0.000 description 16
• 239000004215 Carbon black (E152) Substances 0.000 description 15
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
• 239000003443 antiviral agent Substances 0.000 description 15
• 229940079593 drug Drugs 0.000 description 15
• 229910052938 sodium sulfate Inorganic materials 0.000 description 15
• 235000011152 sodium sulphate Nutrition 0.000 description 15
• 229910052717 sulfur Inorganic materials 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• 235000015165 citric acid Nutrition 0.000 description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
• 238000003756 stirring Methods 0.000 description 14
• 125000001424 substituent group Chemical group 0.000 description 14
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
• 238000006243 chemical reaction Methods 0.000 description 13
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 13
• 150000002148 esters Chemical class 0.000 description 13
• 150000002430 hydrocarbons Chemical class 0.000 description 13
• 238000002953 preparative HPLC Methods 0.000 description 13
• 239000011734 sodium Substances 0.000 description 13
• 239000002904 solvent Substances 0.000 description 13
• BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 12
• 229920000728 polyester Polymers 0.000 description 12
• 238000010992 reflux Methods 0.000 description 12
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
• 241000282412 Homo Species 0.000 description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
• 239000012299 nitrogen atmosphere Substances 0.000 description 11
• 238000005160 1H NMR spectroscopy Methods 0.000 description 10
• JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• 239000003637 basic solution Substances 0.000 description 10
• 230000015572 biosynthetic process Effects 0.000 description 10
• 239000007788 liquid Substances 0.000 description 10
• 238000000926 separation method Methods 0.000 description 10
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
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• 125000006239 protecting group Chemical group 0.000 description 9
• 239000000126 substance Substances 0.000 description 9
• 125000004434 sulfur atom Chemical group 0.000 description 9
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• 206010038997 Retroviral infections Diseases 0.000 description 8
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 8
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• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 8
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• 239000001301 oxygen Substances 0.000 description 8
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 8
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• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
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• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
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• 150000005840 aryl radicals Chemical class 0.000 description 6
• 238000002425 crystallisation Methods 0.000 description 6
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• 125000004122 cyclic group Chemical group 0.000 description 6
• 235000014113 dietary fatty acids Nutrition 0.000 description 6
• XREKLQOUFWBSFH-UHFFFAOYSA-N dimethyl 2-acetylbutanedioate Chemical compound COC(=O)CC(C(C)=O)C(=O)OC XREKLQOUFWBSFH-UHFFFAOYSA-N 0.000 description 6
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• 238000001727 in vivo Methods 0.000 description 6
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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
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• 230000005526 G1 to G0 transition Effects 0.000 description 5
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• LTAGMKMMYIKERY-UHFFFAOYSA-N methyl 2-(2-tert-butyl-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-6,6,6-trifluorohexanoate Chemical compound ClC1=C(C(CCCC(F)(F)F)C(=O)OC)C(C)=NC2=CC(C(C)(C)C)=NN21 LTAGMKMMYIKERY-UHFFFAOYSA-N 0.000 description 2
• HAALVARHZCYMTB-UHFFFAOYSA-N methyl 2-(7-chloro-5-methyl-2-propan-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetate Chemical compound ClC1=C(CC(=O)OC)C(C)=NC2=NC(C(C)C)=NN21 HAALVARHZCYMTB-UHFFFAOYSA-N 0.000 description 2
• HCBLVKLGYJFXNV-UHFFFAOYSA-N methyl 2-[2,3,5-trimethyl-7-(4-methylphenyl)imidazo[4,5-b]pyridin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C1=C(C)N=C2N(C)C(C)=NC2=C1C1=CC=C(C)C=C1 HCBLVKLGYJFXNV-UHFFFAOYSA-N 0.000 description 2
• BGFPXTUNUQXKNS-UHFFFAOYSA-N methyl 2-[2-tert-butyl-3,5-dimethyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=C(C)C(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 BGFPXTUNUQXKNS-UHFFFAOYSA-N 0.000 description 2
• NIAGRZXECTZHFH-UHFFFAOYSA-N methyl 2-[2-tert-butyl-3-chloro-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=C(Cl)C(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 NIAGRZXECTZHFH-UHFFFAOYSA-N 0.000 description 2
• GJXMOQMXFPCOQR-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-3,7-bis(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=C(C=3C=CC(C)=CC=3)C(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 GJXMOQMXFPCOQR-UHFFFAOYSA-N 0.000 description 2
• WWCVLBMDGVZPNV-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(1-methylindol-5-yl)pyrazolo[1,5-a]pyrimidin-6-yl]-3-phenylpropanoate Chemical compound CC1=NC2=CC(C(C)(C)C)=NN2C(C=2C=C3C=CN(C)C3=CC=2)=C1C(C(=O)OC)CC1=CC=CC=C1 WWCVLBMDGVZPNV-UHFFFAOYSA-N 0.000 description 2
• RGNDRPXXEXTNOV-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(4-methylphenyl)-3-phenylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=C(C=3C=CC=CC=3)C(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 RGNDRPXXEXTNOV-UHFFFAOYSA-N 0.000 description 2
• BUCSYAOPYLKVNH-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]-3-phenylpropanoate Chemical compound CC1=NC2=CC(C(C)(C)C)=NN2C(C=2C=CC(C)=CC=2)=C1C(C(=O)OC)CC1=CC=CC=C1 BUCSYAOPYLKVNH-UHFFFAOYSA-N 0.000 description 2
• SUKUSZPNGOMXCX-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]-4-methoxybutanoate Chemical compound COCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 SUKUSZPNGOMXCX-UHFFFAOYSA-N 0.000 description 2
• LGHWMYXWYMFLPH-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(4-propan-2-ylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C(C)C)C=C1 LGHWMYXWYMFLPH-UHFFFAOYSA-N 0.000 description 2
• HBTXVKUHLOUXIR-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C(F)(F)F)C=C1 HBTXVKUHLOUXIR-UHFFFAOYSA-N 0.000 description 2
• QIGJMKVCGDFVCF-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2,3-dihydro-1-benzofuran-5-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound C1=C2OCCC2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(=O)OC)CCC)C(C)(C)C)=C1 QIGJMKVCGDFVCF-UHFFFAOYSA-N 0.000 description 2
• YIVMGSBHAMMRJM-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2,4-difluorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(F)C=C1F YIVMGSBHAMMRJM-UHFFFAOYSA-N 0.000 description 2
• BYWLQYDDMNAOIO-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2,4-dimethylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1C BYWLQYDDMNAOIO-UHFFFAOYSA-N 0.000 description 2
• CZKGLBDANODSRF-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2-chloro-4-methylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1Cl CZKGLBDANODSRF-UHFFFAOYSA-N 0.000 description 2
• LALWJPNZMRVJGW-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2-fluoro-4-methoxyphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(OC)C=C1F LALWJPNZMRVJGW-UHFFFAOYSA-N 0.000 description 2
• PBVUFXFSCIBPFM-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(3,4-dihydro-2h-chromen-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound O1CCCC2=CC(C=3N4N=C(C=C4N=C(C)C=3C(C(=O)OC)CCC)C(C)(C)C)=CC=C21 PBVUFXFSCIBPFM-UHFFFAOYSA-N 0.000 description 2
• ZVIIAYXMQYBWRR-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(4-chloro-2-methoxyphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(Cl)C=C1OC ZVIIAYXMQYBWRR-UHFFFAOYSA-N 0.000 description 2
• DMGWILUXVZJQQB-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(4-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(Cl)C=C1 DMGWILUXVZJQQB-UHFFFAOYSA-N 0.000 description 2
• IUFRCEJOVVRYJS-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(4-ethylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(CC)C=C1 IUFRCEJOVVRYJS-UHFFFAOYSA-N 0.000 description 2
• MWZMBQOCFUAUJT-UHFFFAOYSA-N methyl 2-[5-methyl-7-(4-methylphenyl)-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C=3C=CC=CC=3)=NN2C=1C1=CC=C(C)C=C1 MWZMBQOCFUAUJT-UHFFFAOYSA-N 0.000 description 2
• GTMLZIMJDIHAIS-UHFFFAOYSA-N methyl 2-[7-(1-benzothiophen-5-yl)-2-tert-butyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound C1=C2SC=CC2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(=O)OC)CCC)C(C)(C)C)=C1 GTMLZIMJDIHAIS-UHFFFAOYSA-N 0.000 description 2
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