DE60204452T2 - Pyrazolo[1,5a]Pyridinderivate - Google Patents

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Publication number

DE60204452T2

DE60204452T2 DE60204452T DE60204452T DE60204452T2 DE 60204452 T2 DE60204452 T2 DE 60204452T2 DE 60204452 T DE60204452 T DE 60204452T DE 60204452 T DE60204452 T DE 60204452T DE 60204452 T2 DE60204452 T2 DE 60204452T2

Authority

DE

Germany

Prior art keywords

het

formula

compound

nhr

pyrazolo

Prior art date

2001-04-27

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.)

Expired - Fee Related

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• 150000003222 pyridines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 598
• 238000000034 method Methods 0.000 claims abstract description 107
• 230000008569 process Effects 0.000 claims abstract description 30
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 165
• 125000000217 alkyl group Chemical group 0.000 claims description 136
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 106
• 229910052736 halogen Inorganic materials 0.000 claims description 93
• 150000002367 halogens Chemical class 0.000 claims description 82
• 125000003342 alkenyl group Chemical group 0.000 claims description 75
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 60
• 150000004820 halides Chemical class 0.000 claims description 51
• 125000003118 aryl group Chemical group 0.000 claims description 47
• 125000005843 halogen group Chemical group 0.000 claims description 46
• 238000011282 treatment Methods 0.000 claims description 43
• 125000004429 atom Chemical group 0.000 claims description 42
• 125000001072 heteroaryl group Chemical group 0.000 claims description 41
• 238000002360 preparation method Methods 0.000 claims description 41
• 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 40
• -1 7- (Cyclopentylamino) -3- [2- (cyclopentylamino) -4-pyrimidinyl] -2- (4-fluorophenyl) -N- [2- (4-morpholinyl) ethyl] pyrazolo [1,5-a] pyridine Chemical compound 0.000 claims description 39
• 229910052739 hydrogen Inorganic materials 0.000 claims description 35
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 34
• 238000011321 prophylaxis Methods 0.000 claims description 34
• 150000001412 amines Chemical class 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 32
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 28
• 241001465754 Metazoa Species 0.000 claims description 28
• 201000010099 disease Diseases 0.000 claims description 28
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 25
• 125000000304 alkynyl group Chemical group 0.000 claims description 25
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
• 239000012453 solvate Substances 0.000 claims description 25
• 230000002140 halogenating effect Effects 0.000 claims description 24
• 125000005842 heteroatom Chemical group 0.000 claims description 24
• 239000012038 nucleophile Substances 0.000 claims description 22
• 208000029433 Herpesviridae infectious disease Diseases 0.000 claims description 20
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 20
• 150000002736 metal compounds Chemical class 0.000 claims description 18
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
• 229910052749 magnesium Inorganic materials 0.000 claims description 16
• 230000008878 coupling Effects 0.000 claims description 14
• 238000010168 coupling process Methods 0.000 claims description 14
• 238000005859 coupling reaction Methods 0.000 claims description 14
• 239000003814 drug Substances 0.000 claims description 13
• 238000004519 manufacturing process Methods 0.000 claims description 13
• 239000000460 chlorine Substances 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• ZKYXVDDZBFULBP-UHFFFAOYSA-N n-cyclopentyl-4-[5,7-dichloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(Cl)=CC(Cl)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 ZKYXVDDZBFULBP-UHFFFAOYSA-N 0.000 claims description 9
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 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 8
• MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 8
• 229910052794 bromium Inorganic materials 0.000 claims description 8
• 230000001590 oxidative effect Effects 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 7
• UPURSWNGJDCEHG-UHFFFAOYSA-N n-cyclopentyl-4-[5,7-dichloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C(Cl)=CC(Cl)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 UPURSWNGJDCEHG-UHFFFAOYSA-N 0.000 claims description 7
• 229940093257 valacyclovir Drugs 0.000 claims description 7
• ARFXCYCTFNKRNL-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C(NC2CCCC2)=CC(Cl)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 ARFXCYCTFNKRNL-UHFFFAOYSA-N 0.000 claims description 6
• 229960004150 aciclovir Drugs 0.000 claims description 6
• LNAVWIDITNBXLK-UHFFFAOYSA-N 4-[5-chloro-7-(cyclopentylamino)-3-[2-(cyclopropylamino)pyrimidin-4-yl]pyrazolo[1,5-a]pyridin-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=NN(C(NC2CCCC2)=CC(Cl)=C2)C2=C1C1=CC=NC(NC2CC2)=N1 LNAVWIDITNBXLK-UHFFFAOYSA-N 0.000 claims description 5
• CNMBLWDXHYWTLA-UHFFFAOYSA-N 5-chloro-3-[2-(cyclopentylamino)pyrimidin-4-yl]-n-cyclopropyl-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C(NC2CC2)=CC(Cl)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 CNMBLWDXHYWTLA-UHFFFAOYSA-N 0.000 claims description 5
• GLKWTXUVFUJIGX-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-2-(4-methoxyphenyl)-3-(2-methylsulfanylpyrimidin-4-yl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C(NC2CCCC2)=CC(Cl)=C2)C2=C1C1=CC=NC(SC)=N1 GLKWTXUVFUJIGX-UHFFFAOYSA-N 0.000 claims description 5
• KMUNEVPPFFIIAM-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-2-(4-methoxyphenyl)-3-(2-methylsulfinylpyrimidin-4-yl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C(NC2CCCC2)=CC(Cl)=C2)C2=C1C1=CC=NC(S(C)=O)=N1 KMUNEVPPFFIIAM-UHFFFAOYSA-N 0.000 claims description 5
• RWOYMYIYXMICCH-UHFFFAOYSA-N 7-chloro-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(Cl)=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 RWOYMYIYXMICCH-UHFFFAOYSA-N 0.000 claims description 5
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
• 239000003443 antiviral agent Substances 0.000 claims description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 239000011630 iodine Substances 0.000 claims description 5
• OJDKXSZDDHEORF-UHFFFAOYSA-N n-cyclopentyl-2-(4-fluorophenyl)-3-(2-pyrrolidin-1-ylpyrimidin-4-yl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(NC2CCCC2)=C(C=C2)C(F)(F)F)C2=C1C1=CC=NC(N2CCCC2)=N1 OJDKXSZDDHEORF-UHFFFAOYSA-N 0.000 claims description 5
• JJHWFSQNNDKSJU-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-5-n,7-n-di(propan-2-yl)pyrazolo[1,5-a]pyridine-5,7-diamine Chemical compound C=12C=C(NC(C)C)C=C(NC(C)C)N2N=C(C=2C=CC(F)=CC=2)C=1C(N=1)=CC=NC=1NC1CCCC1 JJHWFSQNNDKSJU-UHFFFAOYSA-N 0.000 claims description 4
• RJAIATRJLAYBKS-UHFFFAOYSA-N 4-[5-chloro-3-[2-(cyclopentylamino)pyrimidin-4-yl]-7-(cyclopropylamino)pyrazolo[1,5-a]pyridin-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=NN(C(NC2CC2)=CC(Cl)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 RJAIATRJLAYBKS-UHFFFAOYSA-N 0.000 claims description 4
• FQXIKSUQXMFWEC-UHFFFAOYSA-N 4-[5-chloro-7-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]pyrazolo[1,5-a]pyridin-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=NN(C(NC2CCCC2)=CC(Cl)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 FQXIKSUQXMFWEC-UHFFFAOYSA-N 0.000 claims description 4
• WCKXXYWOSVAGLZ-UHFFFAOYSA-N 5-chloro-3-[2-(cyclopentylamino)pyrimidin-4-yl]-n-cyclopropyl-2-[4-(cyclopropylmethoxy)phenyl]pyrazolo[1,5-a]pyridin-7-amine Chemical compound N12N=C(C=3C=CC(OCC4CC4)=CC=3)C(C=3N=C(NC4CCCC4)N=CC=3)=C2C=C(Cl)C=C1NC1CC1 WCKXXYWOSVAGLZ-UHFFFAOYSA-N 0.000 claims description 4
• KVWGXHFUCADPDK-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-3-[2-(cyclopropylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C(NC2CCCC2)=CC(Cl)=C2)C2=C1C1=CC=NC(NC2CC2)=N1 KVWGXHFUCADPDK-UHFFFAOYSA-N 0.000 claims description 4
• ZIDVGKZMRABSOF-UHFFFAOYSA-N 7-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n-hydroxypyrazolo[1,5-a]pyridine-6-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=3N=C(NC4CCCC4)N=CC=3)C(C=3C=CC(F)=CC=3)=NN2C=1NC1CCCC1 ZIDVGKZMRABSOF-UHFFFAOYSA-N 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• CRJAQHLKMAMDIH-UHFFFAOYSA-N [7-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-6-yl]-pyrrolidin-1-ylmethanone Chemical compound C1=CC(F)=CC=C1C1=NN(C(NC2CCCC2)=C(C=C2)C(=O)N3CCCC3)C2=C1C1=CC=NC(NC2CCCC2)=N1 CRJAQHLKMAMDIH-UHFFFAOYSA-N 0.000 claims description 4
• FQNJTEQMAQMIMU-UHFFFAOYSA-N [7-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-6-yl]methanol Chemical compound OCC=1C=CC2=C(C=3N=C(NC4CCCC4)N=CC=3)C(C=3C=CC(F)=CC=3)=NN2C=1NC1CCCC1 FQNJTEQMAQMIMU-UHFFFAOYSA-N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• JQTSLEMPHVXCDY-UHFFFAOYSA-N ethyl 7-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-6-carboxylate Chemical compound CCOC(=O)C=1C=CC2=C(C=3N=C(NC4CCCC4)N=CC=3)C(C=3C=CC(F)=CC=3)=NN2C=1NC1CCCC1 JQTSLEMPHVXCDY-UHFFFAOYSA-N 0.000 claims description 4
• AYUKDIIWYYVGRE-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(NC2CCCC2)=C(C=C2)C(F)(F)F)C2=C1C1=CC=NC(NC2CCCC2)=N1 AYUKDIIWYYVGRE-UHFFFAOYSA-N 0.000 claims description 4
• 238000002560 therapeutic procedure Methods 0.000 claims description 4
• HCYHYJMKVPUUIL-UHFFFAOYSA-N 4,6-dibromo-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)=C(Br)C=C2Br)C2=C1C1=CC=NC(NC2CCCC2)=N1 HCYHYJMKVPUUIL-UHFFFAOYSA-N 0.000 claims description 3
• CHYRWZMJWVIPTQ-UHFFFAOYSA-N 4-[5-chloro-2-(4-fluorophenyl)-7-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyridin-3-yl]-n-cyclopentylpyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC(Cl)=CC2=C(C=3N=C(NC4CCCC4)N=CC=3)C(C=3C=CC(F)=CC=3)=NN12 CHYRWZMJWVIPTQ-UHFFFAOYSA-N 0.000 claims description 3
• VJVRRJAEGPKNNL-UHFFFAOYSA-N 4-[5-chloro-2-(4-fluorophenyl)-7-piperidin-1-ylpyrazolo[1,5-a]pyridin-3-yl]-n-cyclopentylpyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(=CC(Cl)=C2)N3CCCCC3)C2=C1C1=CC=NC(NC2CCCC2)=N1 VJVRRJAEGPKNNL-UHFFFAOYSA-N 0.000 claims description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
• WDQYMKZMKUPSGD-UHFFFAOYSA-N 5-chloro-3-[2-(cyclopentylamino)pyrimidin-4-yl]-n-cyclopropyl-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound CC1=CC=CC(C=2C(=C3C=C(Cl)C=C(NC4CC4)N3N=2)C=2N=C(NC3CCCC3)N=CC=2)=C1 WDQYMKZMKUPSGD-UHFFFAOYSA-N 0.000 claims description 3
• KUFDEHIBMUXODJ-UHFFFAOYSA-N 5-chloro-3-[2-(cyclopentylamino)pyrimidin-4-yl]-n-cyclopropyl-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(NC2CC2)=CC(Cl)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 KUFDEHIBMUXODJ-UHFFFAOYSA-N 0.000 claims description 3
• FERZWOQFLPMGHJ-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound CC1=CC=CC(C=2C(=C3C=C(Cl)C=C(NC4CCCC4)N3N=2)C=2N=C(NC3CCCC3)N=CC=2)=C1 FERZWOQFLPMGHJ-UHFFFAOYSA-N 0.000 claims description 3
• FVDIJBUKMLLPCL-UHFFFAOYSA-N 5-chloro-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(Cl)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 FVDIJBUKMLLPCL-UHFFFAOYSA-N 0.000 claims description 3
• UZPCZQJBVPVOLG-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-[4-(cyclopropylmethoxy)phenyl]pyrazolo[1,5-a]pyridin-7-amine Chemical compound N12N=C(C=3C=CC(OCC4CC4)=CC=3)C(C=3N=C(NC4CCCC4)N=CC=3)=C2C=C(Cl)C=C1NC1CCCC1 UZPCZQJBVPVOLG-UHFFFAOYSA-N 0.000 claims description 3
• KRBLXMLDGJHOIF-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-3-[2-(cyclopropylamino)pyrimidin-4-yl]-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound CC1=CC=CC(C=2C(=C3C=C(Cl)C=C(NC4CCCC4)N3N=2)C=2N=C(NC3CC3)N=CC=2)=C1 KRBLXMLDGJHOIF-UHFFFAOYSA-N 0.000 claims description 3
• YPOWBVZTLGEDEB-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-3-[2-(cyclopropylamino)pyrimidin-4-yl]-2-[4-(cyclopropylmethoxy)phenyl]pyrazolo[1,5-a]pyridin-7-amine Chemical compound N12N=C(C=3C=CC(OCC4CC4)=CC=3)C(C=3N=C(NC4CC4)N=CC=3)=C2C=C(Cl)C=C1NC1CCCC1 YPOWBVZTLGEDEB-UHFFFAOYSA-N 0.000 claims description 3
• VFJBIABMTATMLU-UHFFFAOYSA-N 6-chloro-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)=C(Cl)C=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 VFJBIABMTATMLU-UHFFFAOYSA-N 0.000 claims description 3
• UMYIVFMLIMKLIJ-UHFFFAOYSA-N 7-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n,n-dimethylpyrazolo[1,5-a]pyridine-6-carboxamide Chemical compound CN(C)C(=O)C=1C=CC2=C(C=3N=C(NC4CCCC4)N=CC=3)C(C=3C=CC(F)=CC=3)=NN2C=1NC1CCCC1 UMYIVFMLIMKLIJ-UHFFFAOYSA-N 0.000 claims description 3
• TXBSMCXEGQSASW-UHFFFAOYSA-N 7-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-6-carboxylic acid Chemical compound OC(=O)C=1C=CC2=C(C=3N=C(NC4CCCC4)N=CC=3)C(C=3C=CC(F)=CC=3)=NN2C=1NC1CCCC1 TXBSMCXEGQSASW-UHFFFAOYSA-N 0.000 claims description 3
• PXFIELOSJDWIRS-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-5-methoxypyrazolo[1,5-a]pyridin-7-amine Chemical compound N12N=C(C=3C=CC(F)=CC=3)C(C=3N=C(NC4CCCC4)N=CC=3)=C2C=C(OC)C=C1NC1CCCC1 PXFIELOSJDWIRS-UHFFFAOYSA-N 0.000 claims description 3
• OUTDXFTZQARBBK-UHFFFAOYSA-N n-cyclopentyl-4-[5,7-dichloro-2-(3-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound ClC1=CC=CC(C=2C(=C3C=C(Cl)C=C(Cl)N3N=2)C=2N=C(NC3CCCC3)N=CC=2)=C1 OUTDXFTZQARBBK-UHFFFAOYSA-N 0.000 claims description 3
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 3
• NMOLFXVHJPYIJO-UHFFFAOYSA-N 4,6-dibromo-3-[5-bromo-2-(cyclopentylamino)pyrimidin-4-yl]-n-cyclopentyl-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(NC2CCCC2)=C(Br)C=C2Br)C2=C1C1=NC(NC2CCCC2)=NC=C1Br NMOLFXVHJPYIJO-UHFFFAOYSA-N 0.000 claims description 2
• UHYVQIPHBDYTBN-UHFFFAOYSA-N 5-chloro-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n-propan-2-ylpyrazolo[1,5-a]pyridin-7-amine Chemical compound N=1N2C(NC(C)C)=CC(Cl)=CC2=C(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(F)C=C1 UHYVQIPHBDYTBN-UHFFFAOYSA-N 0.000 claims description 2
• BJNRYAGMRQMAFL-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-5-(2-methoxyethoxy)pyrazolo[1,5-a]pyridin-7-amine Chemical compound N12N=C(C=3C=CC(F)=CC=3)C(C=3N=C(NC4CCCC4)N=CC=3)=C2C=C(OCCOC)C=C1NC1CCCC1 BJNRYAGMRQMAFL-UHFFFAOYSA-N 0.000 claims description 2
• FOEMIZSFFWGXHX-UHFFFAOYSA-N 2-methylsulfanylpyrimidine Chemical compound CSC1=NC=CC=N1 FOEMIZSFFWGXHX-UHFFFAOYSA-N 0.000 claims 1
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
• 125000006317 cyclopropyl amino group Chemical group 0.000 claims 1
• DVUBDHRTVYLIPA-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=CC=C21 DVUBDHRTVYLIPA-UHFFFAOYSA-N 0.000 claims 1
• 239000008177 pharmaceutical agent Substances 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 180
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 148
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
• 238000005160 1H NMR spectroscopy Methods 0.000 description 83
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 78
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