JP2004515550A - 治療用化合物 - Google Patents

Info

Publication number

JP2004515550A

JP2004515550A JP2002549679A JP2002549679A JP2004515550A JP 2004515550 A JP2004515550 A JP 2004515550A JP 2002549679 A JP2002549679 A JP 2002549679A JP 2002549679 A JP2002549679 A JP 2002549679A JP 2004515550 A JP2004515550 A JP 2004515550A

Authority

JP

Japan

Prior art keywords

fluorophenyl

pyrazolo

pyridin

amine

pyrimidinyl

Prior art date

2000-12-15

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
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 390
• 230000001225 therapeutic effect Effects 0.000 title description 4
• 238000000034 method Methods 0.000 claims abstract description 90
• 239000003814 drug Substances 0.000 claims abstract description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• 238000002360 preparation method Methods 0.000 claims abstract description 12
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 339
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 262
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 131
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 119
• -1 2-amino-4-pyrimidinyl Chemical group 0.000 claims description 109
• 125000000217 alkyl group Chemical group 0.000 claims description 96
• 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 90
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 87
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 62
• 125000006309 butyl amino group Chemical group 0.000 claims description 54
• 125000005843 halogen group Chemical group 0.000 claims description 49
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 45
• 125000003342 alkenyl group Chemical group 0.000 claims description 45
• 150000001412 amines Chemical class 0.000 claims description 43
• 150000003839 salts Chemical class 0.000 claims description 43
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 40
• 125000005189 alkyl hydroxy group Chemical group 0.000 claims description 36
• 150000003973 alkyl amines Chemical class 0.000 claims description 35
• 239000002904 solvent Substances 0.000 claims description 35
• 241001465754 Metazoa Species 0.000 claims description 33
• 150000005215 alkyl ethers Chemical class 0.000 claims description 33
• 208000029433 Herpesviridae infectious disease Diseases 0.000 claims description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
• 201000010099 disease Diseases 0.000 claims description 28
• 239000012453 solvate Substances 0.000 claims description 27
• 238000011282 treatment Methods 0.000 claims description 27
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
• 125000003118 aryl group Chemical group 0.000 claims description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 22
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 21
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
• 125000005157 alkyl carboxy group Chemical group 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 230000002265 prevention Effects 0.000 claims description 16
• 241000700605 Viruses Species 0.000 claims description 14
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 14
• SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims description 13
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 230000008569 process Effects 0.000 claims description 11
• 241000701044 Human gammaherpesvirus 4 Species 0.000 claims description 10
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 10
• 241000700588 Human alphaherpesvirus 1 Species 0.000 claims description 9
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
• 150000004820 halides Chemical class 0.000 claims description 9
• 241000701022 Cytomegalovirus Species 0.000 claims description 8
• 241000701074 Human alphaherpesvirus 2 Species 0.000 claims description 8
• 241000701027 Human herpesvirus 6 Species 0.000 claims description 8
• MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 8
• 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 8
• HDOVUKNUBWVHOX-QMMMGPOBSA-N Valacyclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)[C@@H](N)C(C)C)C=N2 HDOVUKNUBWVHOX-QMMMGPOBSA-N 0.000 claims description 7
• 229960004150 aciclovir Drugs 0.000 claims description 7
• 230000001590 oxidative effect Effects 0.000 claims description 7
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 7
• XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Natural products NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 7
• 229940093257 valacyclovir Drugs 0.000 claims description 7
• BZRMUMBJGGACCU-UHFFFAOYSA-N 2-(4-bromophenyl)-n-butyl-3-[2-(butylamino)pyrimidin-4-yl]pyrazolo[1,5-a]pyridin-7-amine Chemical compound CCCCNC1=NC=CC(C2=C3C=CC=C(NCCCC)N3N=C2C=2C=CC(Br)=CC=2)=N1 BZRMUMBJGGACCU-UHFFFAOYSA-N 0.000 claims description 6
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
• 208000007514 Herpes zoster Diseases 0.000 claims description 6
• 241000701041 Human betaherpesvirus 7 Species 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 6
• 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 5
• MFNRTZFIEGKCLO-UHFFFAOYSA-N 3-[2-(butylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n-prop-2-enylpyrazolo[1,5-a]pyridin-7-amine Chemical compound CCCCNC1=NC=CC(C2=C3C=CC=C(NCC=C)N3N=C2C=2C=CC(F)=CC=2)=N1 MFNRTZFIEGKCLO-UHFFFAOYSA-N 0.000 claims description 5
• WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims description 5
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
• 241001502974 Human gammaherpesvirus 8 Species 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• QELOEPYXLVHTIO-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(Cl)=CC=C1C1=NN(C(NC2CCCC2)=CC=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 QELOEPYXLVHTIO-UHFFFAOYSA-N 0.000 claims description 4
• TVWMHJOLEDVFFP-UHFFFAOYSA-N 2-(4-fluorophenyl)-3,7-bis(2-fluoropyridin-4-yl)pyrazolo[1,5-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=NN(C(=CC=C2)C=3C=C(F)N=CC=3)C2=C1C1=CC=NC(F)=C1 TVWMHJOLEDVFFP-UHFFFAOYSA-N 0.000 claims description 4
• 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 4
• GYPRSMQRMSLJFX-UHFFFAOYSA-N [6-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-(cyclopentylamino)pyrimidin-4-yl]methanol Chemical compound N=1C(CO)=CC(C2=C3C=CC=C(Cl)N3N=C2C=2C=CC(F)=CC=2)=NC=1NC1CCCC1 GYPRSMQRMSLJFX-UHFFFAOYSA-N 0.000 claims description 4
• 230000000840 anti-viral effect Effects 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
• MBDYVBQWQPYENL-UHFFFAOYSA-N n-butyl-2-(4-fluorophenyl)-3-(2-methylsulfinylpyrimidin-4-yl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound N=1N2C(NCCCC)=CC=CC2=C(C=2N=C(N=CC=2)S(C)=O)C=1C1=CC=C(F)C=C1 MBDYVBQWQPYENL-UHFFFAOYSA-N 0.000 claims description 4
• ZGQFMRKGMPUTDW-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyridin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(NC2CCCC2)=CC=C2)C2=C1C1=CC=NC(NC2CCCC2)=C1 ZGQFMRKGMPUTDW-UHFFFAOYSA-N 0.000 claims description 4
• ZPODCQWVJFCDKN-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(NC2CCCC2)=CC=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 ZPODCQWVJFCDKN-UHFFFAOYSA-N 0.000 claims description 4
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
• HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims description 4
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
• QDZOJLCCONWJLX-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-iodo-3-pyridin-4-ylpyrazolo[1,5-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=NN(C(I)=CC=C2)C2=C1C1=CC=NC=C1 QDZOJLCCONWJLX-UHFFFAOYSA-N 0.000 claims description 3
• PPLLZTCPKKKXMG-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-(1-methylpyrrolidin-2-yl)ethyl]-3-pyridin-4-ylpyrazolo[1,5-a]pyridin-7-amine Chemical compound CN1CCCC1CCNC1=CC=CC2=C(C=3C=CN=CC=3)C(C=3C=CC(F)=CC=3)=NN12 PPLLZTCPKKKXMG-UHFFFAOYSA-N 0.000 claims description 3
• MTUPINQDZNXFAG-UHFFFAOYSA-N 2-[[3-[2-(cyclopentylamino)-6-methylpyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-yl]amino]acetic acid Chemical compound N=1C(C)=CC(C2=C3C=CC=C(NCC(O)=O)N3N=C2C=2C=CC(F)=CC=2)=NC=1NC1CCCC1 MTUPINQDZNXFAG-UHFFFAOYSA-N 0.000 claims description 3
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 3
• GMUUSVOJOHJMLL-UHFFFAOYSA-N 3-[2-(butylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n-(2-methoxyethyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound CCCCNC1=NC=CC(C2=C3C=CC=C(NCCOC)N3N=C2C=2C=CC(F)=CC=2)=N1 GMUUSVOJOHJMLL-UHFFFAOYSA-N 0.000 claims description 3
• PVPVPEUVKPDJFD-UHFFFAOYSA-N 3-[2-(butylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n-methylpyrazolo[1,5-a]pyridin-7-amine Chemical compound CCCCNC1=NC=CC(C2=C3C=CC=C(NC)N3N=C2C=2C=CC(F)=CC=2)=N1 PVPVPEUVKPDJFD-UHFFFAOYSA-N 0.000 claims description 3
• HWWATJDGLHIOIC-UHFFFAOYSA-N 3-[2-(butylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n-propylpyrazolo[1,5-a]pyridin-7-amine Chemical compound CCCCNC1=NC=CC(C2=C3C=CC=C(NCCC)N3N=C2C=2C=CC(F)=CC=2)=N1 HWWATJDGLHIOIC-UHFFFAOYSA-N 0.000 claims description 3
• DJQUIJVLWKXCPL-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound N=1N2C(N)=CC=CC2=C(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(F)C=C1 DJQUIJVLWKXCPL-UHFFFAOYSA-N 0.000 claims description 3
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• UMBKZMBLMSTZKH-UHFFFAOYSA-N 6-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-(cyclopentylamino)pyrimidine-4-carboxylic acid Chemical compound N=1C(C(=O)O)=CC(C2=C3C=CC=C(Cl)N3N=C2C=2C=CC(F)=CC=2)=NC=1NC1CCCC1 UMBKZMBLMSTZKH-UHFFFAOYSA-N 0.000 claims description 3
• MKMQOVQANWMIIT-UHFFFAOYSA-N 7-bromo-2-(4-fluorophenyl)-3-pyridin-4-ylpyrazolo[1,5-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=NN(C(Br)=CC=C2)C2=C1C1=CC=NC=C1 MKMQOVQANWMIIT-UHFFFAOYSA-N 0.000 claims description 3
• NMGBNZIPZPBKAJ-UHFFFAOYSA-N [2-(cyclopentylamino)-6-[7-(cyclopentylamino)-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-4-yl]methanol Chemical compound N=1C(CO)=CC(C2=C3C=CC=C(NC4CCCC4)N3N=C2C=2C=CC(F)=CC=2)=NC=1NC1CCCC1 NMGBNZIPZPBKAJ-UHFFFAOYSA-N 0.000 claims description 3
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 3
• 125000002346 iodo group Chemical group I* 0.000 claims description 3
• BNIPJZUJUWWJMR-UHFFFAOYSA-N n-butyl-2-(4-fluorophenyl)-3-pyridin-4-ylpyrazolo[1,5-a]pyridin-7-amine Chemical compound N=1N2C(NCCCC)=CC=CC2=C(C=2C=CN=CC=2)C=1C1=CC=C(F)C=C1 BNIPJZUJUWWJMR-UHFFFAOYSA-N 0.000 claims description 3
• XXUMHEXVTRQQTL-UHFFFAOYSA-N n-butyl-4-[2-(4-fluorophenyl)-7-(furan-2-yl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CCCCNC1=NC=CC(C2=C3C=CC=C(N3N=C2C=2C=CC(F)=CC=2)C=2OC=CC=2)=N1 XXUMHEXVTRQQTL-UHFFFAOYSA-N 0.000 claims description 3
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 3
• 238000002560 therapeutic procedure Methods 0.000 claims description 3
• KJUKBZFXBJVVKE-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-methyl-3-pyridin-4-ylpyrazolo[1,5-a]pyridin-7-amine Chemical compound N=1N2C(NC)=CC=CC2=C(C=2C=CN=CC=2)C=1C1=CC=C(F)C=C1 KJUKBZFXBJVVKE-UHFFFAOYSA-N 0.000 claims description 2
• AGHBQALSJZKTMH-UHFFFAOYSA-N 3-[[4-[7-(butylamino)-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-yl]amino]propan-1-ol Chemical compound N=1N2C(NCCCC)=CC=CC2=C(C=2N=C(NCCCO)N=CC=2)C=1C1=CC=C(F)C=C1 AGHBQALSJZKTMH-UHFFFAOYSA-N 0.000 claims description 2
• PYLRHIDDAWYMMF-UHFFFAOYSA-N 4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-n-cyclopentyl-5-methylpyrimidin-2-amine Chemical compound N1=C(C2=C3C=CC=C(Cl)N3N=C2C=2C=CC(F)=CC=2)C(C)=CN=C1NC1CCCC1 PYLRHIDDAWYMMF-UHFFFAOYSA-N 0.000 claims description 2
• LRSNFQBSTKTYKI-UHFFFAOYSA-N 6-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-n-cyclopentyl-2-(cyclopentylamino)pyrimidine-4-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NN(C(Cl)=CC=C2)C2=C1C1=CC(C(=O)NC2CCCC2)=NC(NC2CCCC2)=N1 LRSNFQBSTKTYKI-UHFFFAOYSA-N 0.000 claims description 2
• VKZZXFMSDDDGAV-UHFFFAOYSA-N 7-chloro-2-(4-fluorophenyl)-3-(2-phenylpyrimidin-4-yl)pyrazolo[1,5-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=NN(C(Cl)=CC=C2)C2=C1C1=CC=NC(C=2C=CC=CC=2)=N1 VKZZXFMSDDDGAV-UHFFFAOYSA-N 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• CEJCMEFOUUNONM-UHFFFAOYSA-N n,n-diethyl-2-(4-fluorophenyl)-3-pyridin-4-ylpyrazolo[1,5-a]pyridin-7-amine Chemical compound N=1N2C(N(CC)CC)=CC=CC2=C(C=2C=CN=CC=2)C=1C1=CC=C(F)C=C1 CEJCMEFOUUNONM-UHFFFAOYSA-N 0.000 claims description 2
• CDFZKTOECHOGJW-UHFFFAOYSA-N n-cyclopentyl-2-(4-fluorophenyl)-3-(2-hydrazinylpyridin-4-yl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=NC(NN)=CC(C2=C3C=CC=C(NC4CCCC4)N3N=C2C=2C=CC(F)=CC=2)=C1 CDFZKTOECHOGJW-UHFFFAOYSA-N 0.000 claims description 2
• MPLQLGYBGSLDNE-UHFFFAOYSA-N n-cyclopentyl-2-(4-fluorophenyl)-3-pyridin-4-ylpyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(NC2CCCC2)=CC=C2)C2=C1C1=CC=NC=C1 MPLQLGYBGSLDNE-UHFFFAOYSA-N 0.000 claims description 2
• ZZMXDTJHYHXNBR-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)-6-[(dimethylamino)methyl]pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound N=1C(CN(C)C)=CC(C2=C3C=CC=C(NC4CCCC4)N3N=C2C=2C=CC(F)=CC=2)=NC=1NC1CCCC1 ZZMXDTJHYHXNBR-UHFFFAOYSA-N 0.000 claims description 2
• 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
• 101100079984 Caenorhabditis elegans nhr-9 gene Proteins 0.000 claims 1
• 125000005518 carboxamido group Chemical group 0.000 claims 1
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 340
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 156
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 150
• 238000005160 1H NMR spectroscopy Methods 0.000 description 121
• 239000007787 solid Substances 0.000 description 104
• 239000000243 solution Substances 0.000 description 96
• 239000000203 mixture Substances 0.000 description 88
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 86
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 70
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 68
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 62
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 60
• 238000004293 19F NMR spectroscopy Methods 0.000 description 53
• 239000002585 base Substances 0.000 description 44
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
• 238000006243 chemical reaction Methods 0.000 description 39
• ATENWFZPEVYXTK-UHFFFAOYSA-N 7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=NN2C(Cl)=CC=CC2=C1 ATENWFZPEVYXTK-UHFFFAOYSA-N 0.000 description 38
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