CA2821819A1 - 6-substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders - Google Patents

Info

Publication number

CA2821819A1

CA2821819A1 CA2821819A CA2821819A CA2821819A1 CA 2821819 A1 CA2821819 A1 CA 2821819A1 CA 2821819 A CA2821819 A CA 2821819A CA 2821819 A CA2821819 A CA 2821819A CA 2821819 A1 CA2821819 A1 CA 2821819A1

Authority

CA

Canada

Prior art keywords

alkyl

amino

pyrazin

cyclopropyl

imidazo

Prior art date

2010-12-17

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 238000011282 treatment Methods 0.000 title claims abstract description 37
• -1 6-substituted imidazopyrazines Chemical class 0.000 title claims description 290
• 230000003463 hyperproliferative effect Effects 0.000 title abstract description 7
• 239000003112 inhibitor Substances 0.000 title description 15
• 150000001875 compounds Chemical class 0.000 claims abstract description 296
• 238000000034 method Methods 0.000 claims abstract description 77
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 53
• 201000010099 disease Diseases 0.000 claims abstract description 31
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
• 238000011321 prophylaxis Methods 0.000 claims abstract description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 235
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 169
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 145
• 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 123
• 125000001072 heteroaryl group Chemical group 0.000 claims description 113
• 239000000203 mixture Substances 0.000 claims description 111
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 90
• 238000002360 preparation method Methods 0.000 claims description 75
• 206010028980 Neoplasm Diseases 0.000 claims description 68
• 125000005843 halogen group Chemical group 0.000 claims description 66
• 229910052739 hydrogen Inorganic materials 0.000 claims description 66
• 125000003118 aryl group Chemical group 0.000 claims description 63
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 63
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 56
• 150000003839 salts Chemical class 0.000 claims description 56
• 239000001257 hydrogen Substances 0.000 claims description 55
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 55
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 51
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 44
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 43
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 36
• 125000004432 carbon atom Chemical group C* 0.000 claims description 32
• 239000012453 solvate Substances 0.000 claims description 29
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 26
• 125000005418 aryl aryl group Chemical group 0.000 claims description 26
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 23
• 150000001204 N-oxides Chemical class 0.000 claims description 22
• 229910052799 carbon Inorganic materials 0.000 claims description 22
• 150000002148 esters Chemical class 0.000 claims description 20
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 18
• 150000002431 hydrogen Chemical class 0.000 claims description 17
• 206010027476 Metastases Diseases 0.000 claims description 16
• 230000024932 T cell mediated immunity Effects 0.000 claims description 15
• 230000001413 cellular effect Effects 0.000 claims description 15
• 230000028709 inflammatory response Effects 0.000 claims description 15
• 230000010261 cell growth Effects 0.000 claims description 14
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 14
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 10
• 239000000460 chlorine Substances 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 9
• 208000032839 leukemia Diseases 0.000 claims description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 8
• 206010025323 Lymphomas Diseases 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• 125000000524 functional group Chemical group 0.000 claims description 7
• 229910052740 iodine Inorganic materials 0.000 claims description 7
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 230000002496 gastric effect Effects 0.000 claims description 6
• 201000010536 head and neck cancer Diseases 0.000 claims description 6
• 230000001404 mediated effect Effects 0.000 claims description 6
• 210000002307 prostate Anatomy 0.000 claims description 6
• 206010059282 Metastases to central nervous system Diseases 0.000 claims description 5
• 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 5
• 206010029098 Neoplasm skin Diseases 0.000 claims description 5
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 5
• 210000000038 chest Anatomy 0.000 claims description 5
• 230000002124 endocrine Effects 0.000 claims description 5
• 208000037841 lung tumor Diseases 0.000 claims description 5
• 201000004477 skin sarcoma Diseases 0.000 claims description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• 102100036109 Dual specificity protein kinase TTK Human genes 0.000 claims description 4
• 101000659223 Homo sapiens Dual specificity protein kinase TTK Proteins 0.000 claims description 4
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
• ZBWCTUFKOQUIET-UHFFFAOYSA-N 3-[4-(cyclopropylcarbamoyl)phenyl]-8-(2-methylpropylamino)-n-phenylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C(=O)NC=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 ZBWCTUFKOQUIET-UHFFFAOYSA-N 0.000 claims description 2
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 2
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
• OJHYRKGXJUEHOM-UHFFFAOYSA-N n-cyclopropyl-4-[6-phenyl-8-(prop-2-enylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC=C)=NC(C=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 OJHYRKGXJUEHOM-UHFFFAOYSA-N 0.000 claims description 2
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
• 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims 1
• XFUKMNRTGAUAAV-UHFFFAOYSA-N 2-[3-[3-[4-(cyclopropylcarbamoyl)phenyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-6-yl]phenyl]acetic acid Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3C=C(CC(O)=O)C=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 XFUKMNRTGAUAAV-UHFFFAOYSA-N 0.000 claims 1
• DJLVOBOHNARWRH-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3CCOCC=3)=CN2C=1C(C=C1Cl)=CC=C1C(=O)NC1CC1 DJLVOBOHNARWRH-UHFFFAOYSA-N 0.000 claims 1
• ULYXTUBELQXLKE-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCCC(F)(F)F)=NC(C=3CCOCC=3)=CN2C=1C(C=C1Cl)=CC=C1C(=O)NC1CC1 ULYXTUBELQXLKE-UHFFFAOYSA-N 0.000 claims 1
• GCUNVXJKOGAKHW-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-(oxolan-2-ylmethylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound ClC1=CC(C=2N3C=C(N=C(NCC4OCCC4)C3=NC=2)C=2CCOCC=2)=CC=C1C(=O)NC1CC1 GCUNVXJKOGAKHW-UHFFFAOYSA-N 0.000 claims 1
• CBBMOOCLRAKQHC-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[6-(furan-3-yl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C3=COC=C3)=CN2C=1C(C=C1Cl)=CC=C1C(=O)NC1CC1 CBBMOOCLRAKQHC-UHFFFAOYSA-N 0.000 claims 1
• DNSQINPCHMGYCC-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[6-(furan-3-yl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCCC(F)(F)F)=NC(C3=COC=C3)=CN2C=1C(C=C1Cl)=CC=C1C(=O)NC1CC1 DNSQINPCHMGYCC-UHFFFAOYSA-N 0.000 claims 1
• NDMZAGXJYIDQFF-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[6-(furan-3-yl)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)(O)C)=NC(C3=COC=C3)=CN2C=1C(C=C1Cl)=CC=C1C(=O)NC1CC1 NDMZAGXJYIDQFF-UHFFFAOYSA-N 0.000 claims 1
• NJKBPPSXAZIRRD-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[6-(furan-3-yl)-8-[(2-methylpyrazol-3-yl)methylamino]imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CN1N=CC=C1CNC1=NC(C2=COC=C2)=CN2C1=NC=C2C(C=C1Cl)=CC=C1C(=O)NC1CC1 NJKBPPSXAZIRRD-UHFFFAOYSA-N 0.000 claims 1
• JXVVAWJMSUGUSZ-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[6-pyridin-4-yl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCCC(F)(F)F)=NC(C=3C=CN=CC=3)=CN2C=1C(C=C1Cl)=CC=C1C(=O)NC1CC1 JXVVAWJMSUGUSZ-UHFFFAOYSA-N 0.000 claims 1
• WKXXNKOYGJTXIX-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[8-(2-methylpropylamino)-6-(1h-pyrazol-5-yl)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3NN=CC=3)=CN2C=1C(C=C1Cl)=CC=C1C(=O)NC1CC1 WKXXNKOYGJTXIX-UHFFFAOYSA-N 0.000 claims 1
• WPQTWTGESDILER-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[8-(2-methylpropylamino)-6-pyridin-4-ylimidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3C=CN=CC=3)=CN2C=1C(C=C1Cl)=CC=C1C(=O)NC1CC1 WPQTWTGESDILER-UHFFFAOYSA-N 0.000 claims 1
• ONRSYURALJASOR-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[8-(oxolan-2-ylmethylamino)-6-(1h-pyrazol-5-yl)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound ClC1=CC(C=2N3C=C(N=C(NCC4OCCC4)C3=NC=2)C=2NN=CC=2)=CC=C1C(=O)NC1CC1 ONRSYURALJASOR-UHFFFAOYSA-N 0.000 claims 1
• SFWPVNRYSZRWNE-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[8-[(2-methylpyrazol-3-yl)methylamino]-6-(1h-pyrazol-5-yl)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CN1N=CC=C1CNC1=NC(C=2NN=CC=2)=CN2C1=NC=C2C(C=C1Cl)=CC=C1C(=O)NC1CC1 SFWPVNRYSZRWNE-UHFFFAOYSA-N 0.000 claims 1
• UEVUEELTZKCKJV-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[8-[(2-methylpyrazol-3-yl)methylamino]-6-pyridin-4-ylimidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CN1N=CC=C1CNC1=NC(C=2C=CN=CC=2)=CN2C1=NC=C2C(C=C1Cl)=CC=C1C(=O)NC1CC1 UEVUEELTZKCKJV-UHFFFAOYSA-N 0.000 claims 1
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
• QCGYICFOJINCDA-UHFFFAOYSA-N 3-[4-(cyclopropylcarbamoyl)phenyl]-8-(2-methylpropylamino)-n-(2-piperidin-1-ylethyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C(=O)NCCN3CCCCC3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 QCGYICFOJINCDA-UHFFFAOYSA-N 0.000 claims 1
• BRCUKIFKMZQOBJ-UHFFFAOYSA-N 3-[4-(cyclopropylcarbamoyl)phenyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C(N)=O)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 BRCUKIFKMZQOBJ-UHFFFAOYSA-N 0.000 claims 1
• MIYZOJSYSDDHJX-UHFFFAOYSA-N 4-[6-(1-benzothiophen-2-yl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3SC4=CC=CC=C4C=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 MIYZOJSYSDDHJX-UHFFFAOYSA-N 0.000 claims 1
• XANWOTAUQBJGKY-UHFFFAOYSA-N 4-[6-(1-benzothiophen-3-yl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3C4=CC=CC=C4SC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 XANWOTAUQBJGKY-UHFFFAOYSA-N 0.000 claims 1
• XCHHMNGBGBWKLW-UHFFFAOYSA-N 4-[6-(2-chloropyridin-4-yl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3C=C(Cl)N=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 XCHHMNGBGBWKLW-UHFFFAOYSA-N 0.000 claims 1
• HJZALJJLSSOMEQ-UHFFFAOYSA-N 4-[6-(6-acetamidopyridin-3-yl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3C=NC(NC(C)=O)=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 HJZALJJLSSOMEQ-UHFFFAOYSA-N 0.000 claims 1
• BJQNKGAUQSTCRM-UHFFFAOYSA-N 4-[6-(aminomethyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=C(CN)N=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 BJQNKGAUQSTCRM-UHFFFAOYSA-N 0.000 claims 1
• CPSKJUGLVCYCAJ-UHFFFAOYSA-N 4-[6-(anilinomethyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=C(CNC=4C=CC=CC=4)N=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 CPSKJUGLVCYCAJ-UHFFFAOYSA-N 0.000 claims 1
• IUQLUGLNWGOKSP-UHFFFAOYSA-N 4-[6-[3-(2-amino-2-oxoethyl)-4-methylphenyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3C=C(CC(N)=O)C(C)=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 IUQLUGLNWGOKSP-UHFFFAOYSA-N 0.000 claims 1
• VBXZDMZTVCMSJL-UHFFFAOYSA-N 4-[6-[3-(2-amino-2-oxoethyl)-4-methylphenyl]-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C1=C(CC(N)=O)C(C)=CC=C1C(N=C1NCC(C)(C)O)=CN2C1=NC=C2C1=CC=C(C(=O)NC2CC2)C=C1 VBXZDMZTVCMSJL-UHFFFAOYSA-N 0.000 claims 1
• IAGYWVUIFQWFJN-UHFFFAOYSA-N 4-[6-[3-(2-amino-2-oxoethyl)phenyl]-8-(2-cyanoethylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound NC(=O)CC1=CC=CC(C=2N=C(NCCC#N)C3=NC=C(N3C=2)C=2C=CC(=CC=2)C(=O)NC2CC2)=C1 IAGYWVUIFQWFJN-UHFFFAOYSA-N 0.000 claims 1
• BRXLAKYYEUPFAY-UHFFFAOYSA-N 4-[6-[3-(2-amino-2-oxoethyl)phenyl]-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCC(C)(O)C)=NC(C=3C=C(CC(N)=O)C=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 BRXLAKYYEUPFAY-UHFFFAOYSA-N 0.000 claims 1
• PQBCSCUSLGGJFT-UHFFFAOYSA-N 4-[6-cyano-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C#N)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 PQBCSCUSLGGJFT-UHFFFAOYSA-N 0.000 claims 1
• YBUGFYLNDZHNIS-UHFFFAOYSA-N 4-[8-(3-aminopropylamino)-6-pyridin-4-ylimidazo[1,2-a]pyrazin-3-yl]-2-chloro-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCCCN)=NC(C=3C=CN=CC=3)=CN2C=1C(C=C1Cl)=CC=C1C(=O)NC1CC1 YBUGFYLNDZHNIS-UHFFFAOYSA-N 0.000 claims 1
• MEKPDTMLCHWCAJ-UHFFFAOYSA-N 4-[8-(4-aminobutylamino)-6-[3-(2-amino-2-oxoethyl)phenyl]imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCCCCN)=NC(C=3C=C(CC(N)=O)C=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 MEKPDTMLCHWCAJ-UHFFFAOYSA-N 0.000 claims 1
• WZJQMEBEDUXGGV-UHFFFAOYSA-N 4-[8-(5-aminopent-3-ynylamino)-6-phenylimidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCCC#CCN)=NC(C=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 WZJQMEBEDUXGGV-UHFFFAOYSA-N 0.000 claims 1
• FDJGSBITVOEQSL-UHFFFAOYSA-N 4-[8-[(5-chlorothiophen-2-yl)methylamino]-6-pyridin-4-ylimidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound S1C(Cl)=CC=C1CNC1=NC(C=2C=CN=CC=2)=CN2C1=NC=C2C1=CC=C(C(=O)NC2CC2)C=C1 FDJGSBITVOEQSL-UHFFFAOYSA-N 0.000 claims 1
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 1
• KFEXWAJFVDUWFW-UHFFFAOYSA-N n-(2,2-dimethylcyclopropyl)-4-[8-(2-methylpropylamino)-6-phenylimidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3C=CC=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1(C)C KFEXWAJFVDUWFW-UHFFFAOYSA-N 0.000 claims 1
• NWFSDPBOIPALDK-UHFFFAOYSA-N n-cyclopropyl-2-fluoro-4-[6-(furan-3-yl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound FC1=CC(C=2N3C=C(N=C(NCCC(F)(F)F)C3=NC=2)C2=COC=C2)=CC=C1C(=O)NC1CC1 NWFSDPBOIPALDK-UHFFFAOYSA-N 0.000 claims 1
• FHEZBKRVZQHMCX-UHFFFAOYSA-N n-cyclopropyl-2-fluoro-4-[6-(furan-3-yl)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)(O)C)=NC(C3=COC=C3)=CN2C=1C(C=C1F)=CC=C1C(=O)NC1CC1 FHEZBKRVZQHMCX-UHFFFAOYSA-N 0.000 claims 1
• QZKLSKGGQAVCNO-UHFFFAOYSA-N n-cyclopropyl-2-fluoro-4-[6-pyridin-4-yl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound FC1=CC(C=2N3C=C(N=C(NCCC(F)(F)F)C3=NC=2)C=2C=CN=CC=2)=CC=C1C(=O)NC1CC1 QZKLSKGGQAVCNO-UHFFFAOYSA-N 0.000 claims 1
• SNDKMRXILLFHAP-UHFFFAOYSA-N n-cyclopropyl-2-fluoro-4-[8-(2-methylpropylamino)-6-(1h-pyrazol-5-yl)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3NN=CC=3)=CN2C=1C(C=C1F)=CC=C1C(=O)NC1CC1 SNDKMRXILLFHAP-UHFFFAOYSA-N 0.000 claims 1
• IALPHRPPYXYRFH-UHFFFAOYSA-N n-cyclopropyl-2-fluoro-4-[8-(2-methylpropylamino)-6-pyridin-4-ylimidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3C=CN=CC=3)=CN2C=1C(C=C1F)=CC=C1C(=O)NC1CC1 IALPHRPPYXYRFH-UHFFFAOYSA-N 0.000 claims 1
• OVZFHFQKOTTYND-UHFFFAOYSA-N n-cyclopropyl-2-fluoro-4-[8-(oxolan-2-ylmethylamino)-6-(1h-pyrazol-5-yl)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound FC1=CC(C=2N3C=C(N=C(NCC4OCCC4)C3=NC=2)C=2NN=CC=2)=CC=C1C(=O)NC1CC1 OVZFHFQKOTTYND-UHFFFAOYSA-N 0.000 claims 1
• PRBOMSHMXYSCFA-UHFFFAOYSA-N n-cyclopropyl-2-fluoro-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(1h-pyrazol-5-yl)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)(O)C)=NC(C=3NN=CC=3)=CN2C=1C(C=C1F)=CC=C1C(=O)NC1CC1 PRBOMSHMXYSCFA-UHFFFAOYSA-N 0.000 claims 1
• PUCADTHHSNEBMX-UHFFFAOYSA-N n-cyclopropyl-2-fluoro-4-[8-[(2-methylpyrazol-3-yl)methylamino]-6-(1h-pyrazol-5-yl)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CN1N=CC=C1CNC1=NC(C=2NN=CC=2)=CN2C1=NC=C2C(C=C1F)=CC=C1C(=O)NC1CC1 PUCADTHHSNEBMX-UHFFFAOYSA-N 0.000 claims 1
• HKMQSDMIYAOWNO-UHFFFAOYSA-N n-cyclopropyl-2-fluoro-4-[8-[(2-methylpyrazol-3-yl)methylamino]-6-pyridin-4-ylimidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CN1N=CC=C1CNC1=NC(C=2C=CN=CC=2)=CN2C1=NC=C2C(C=C1F)=CC=C1C(=O)NC1CC1 HKMQSDMIYAOWNO-UHFFFAOYSA-N 0.000 claims 1
• YCWVFXJWADCHBF-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(1,2,3,6-tetrahydropyridin-4-yl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3C=C(N=C(NCCC(F)(F)F)C3=NC=2)C=2CCNCC=2)=CC=C1C(=O)NC1CC1 YCWVFXJWADCHBF-UHFFFAOYSA-N 0.000 claims 1
• KORRCUBHCFDXMO-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(1-methylpyrazol-4-yl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3C=C(N=C(NCCC(F)(F)F)C3=NC=2)C2=CN(C)N=C2)=CC=C1C(=O)NC1CC1 KORRCUBHCFDXMO-UHFFFAOYSA-N 0.000 claims 1
• BQPDWACUQTXRMS-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(1-methylpyrrol-2-yl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3C=C(N=C(NCCC(F)(F)F)C3=NC=2)C=2N(C=CC=2)C)=CC=C1C(=O)NC1CC1 BQPDWACUQTXRMS-UHFFFAOYSA-N 0.000 claims 1
• GXJVHBAQQSXHIZ-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(1-oxo-3,6-dihydro-2h-thiopyran-4-yl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3C=C(N=C(NCCC(F)(F)F)C3=NC=2)C=2CCS(=O)CC=2)=CC=C1C(=O)NC1CC1 GXJVHBAQQSXHIZ-UHFFFAOYSA-N 0.000 claims 1
• QXNITFIMNSTWIP-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(2-methylpyrazol-3-yl)-8-[(3,3,3-trifluoro-2-hydroxypropyl)amino]imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3C=C(N=C(NCC(O)C(F)(F)F)C3=NC=2)C=2N(N=CC=2)C)=CC=C1C(=O)NC1CC1 QXNITFIMNSTWIP-UHFFFAOYSA-N 0.000 claims 1
• KGWJVBSXAGQIDT-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(2-methylpyridin-4-yl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C1=NC(C)=CC(C=2N=C(NCCC(F)(F)F)C3=NC=C(N3C=2)C=2C=C(C)C(C(=O)NC3CC3)=CC=2)=C1 KGWJVBSXAGQIDT-UHFFFAOYSA-N 0.000 claims 1
• DTWCCBLGGIEOIF-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(piperidin-1-ylmethyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3C=C(CN4CCCCC4)N=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 DTWCCBLGGIEOIF-UHFFFAOYSA-N 0.000 claims 1
• FPYWIVXQQLAWEZ-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-phenoxy-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3C=C(OC=4C=CC=CC=4)N=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 FPYWIVXQQLAWEZ-UHFFFAOYSA-N 0.000 claims 1
• ILALDQIOCPLJIQ-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-phenylsulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3C=C(SC=4C=CC=CC=4)N=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 ILALDQIOCPLJIQ-UHFFFAOYSA-N 0.000 claims 1
• VVQQEUZUJJOGNQ-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-pyridin-3-yl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3C=C(N=C(NCCC(F)(F)F)C3=NC=2)C=2C=NC=CC=2)=CC=C1C(=O)NC1CC1 VVQQEUZUJJOGNQ-UHFFFAOYSA-N 0.000 claims 1
• URBYIEBMCNNMGO-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[8-(2-methylpropylamino)-6-pyridin-4-ylimidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3C=CN=CC=3)=CN2C=1C(C=C1C)=CC=C1C(=O)NC1CC1 URBYIEBMCNNMGO-UHFFFAOYSA-N 0.000 claims 1
• GWXQNSWURCIHQT-UHFFFAOYSA-N n-cyclopropyl-4-[6-(1,1-dioxothiazinan-2-yl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(N3S(CCCC3)(=O)=O)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 GWXQNSWURCIHQT-UHFFFAOYSA-N 0.000 claims 1
• OMQNBDPPSUIEFO-UHFFFAOYSA-N n-cyclopropyl-4-[6-(1-methylindol-5-yl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3C=C4C=CN(C)C4=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 OMQNBDPPSUIEFO-UHFFFAOYSA-N 0.000 claims 1
• HOOIOMVEEXYEJV-UHFFFAOYSA-N n-cyclopropyl-4-[6-(1-methylpiperidin-4-yl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C3CCN(C)CC3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 HOOIOMVEEXYEJV-UHFFFAOYSA-N 0.000 claims 1
• KCBAFKWXINELNG-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]-2-fluorobenzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3CCOCC=3)=CN2C=1C(C=C1F)=CC=C1C(=O)NC1CC1 KCBAFKWXINELNG-UHFFFAOYSA-N 0.000 claims 1
• XUQADVVNTUXOIU-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3CCOCC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 XUQADVVNTUXOIU-UHFFFAOYSA-N 0.000 claims 1
• KTZYJNPVBBCGRU-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-(4-hydroxypentylamino)imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound C=1N=C2C(NCCCC(O)C)=NC(C=3CCOCC=3)=CN2C=1C(C=C1C)=CC=C1C(=O)NC1CC1 KTZYJNPVBBCGRU-UHFFFAOYSA-N 0.000 claims 1
• XMXOBANUNMXGOK-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-(oxolan-3-ylmethylamino)imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=C(N=C(NCC4COCC4)C3=NC=2)C=2CCOCC=2)=CC=C1C(=O)NC1CC1 XMXOBANUNMXGOK-UHFFFAOYSA-N 0.000 claims 1
• UOAQBBFOTVOXJV-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-[(1-ethylpyrrolidin-3-yl)methylamino]imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound C1N(CC)CCC1CNC1=NC(C=2CCOCC=2)=CN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 UOAQBBFOTVOXJV-UHFFFAOYSA-N 0.000 claims 1
• XUDBXKRVKNSWMN-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-[(1-methyl-5-oxopyrrolidin-3-yl)methylamino]imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound C1C(=O)N(C)CC1CNC1=NC(C=2CCOCC=2)=CN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 XUDBXKRVKNSWMN-UHFFFAOYSA-N 0.000 claims 1
• HJOCMQHAVSRGJA-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-[(1-methylpyrrolidin-3-yl)methylamino]imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound C1N(C)CCC1CNC1=NC(C=2CCOCC=2)=CN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 HJOCMQHAVSRGJA-UHFFFAOYSA-N 0.000 claims 1
• XCAHJHQFTCXLQP-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl]-2-fluorobenzamide Chemical compound C=1N=C2C(NCC(C)(O)C)=NC(C=3CCOCC=3)=CN2C=1C(C=C1F)=CC=C1C(=O)NC1CC1 XCAHJHQFTCXLQP-UHFFFAOYSA-N 0.000 claims 1
• FRIJYYWCHAURLF-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=C(N=C(NCC(C)(C)O)C3=NC=2)C=2CCOCC=2)=CC=C1C(=O)NC1CC1 FRIJYYWCHAURLF-UHFFFAOYSA-N 0.000 claims 1
• MOFGNSZOUCRDAX-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-[(2-methylcyclopropyl)methylamino]imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound CC1CC1CNC1=NC(C=2CCOCC=2)=CN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 MOFGNSZOUCRDAX-UHFFFAOYSA-N 0.000 claims 1
• BUMVFGYLRJBZDM-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-[(2-methylpyrazol-3-yl)methylamino]imidazo[1,2-a]pyrazin-3-yl]-2-fluorobenzamide Chemical compound CN1N=CC=C1CNC1=NC(C=2CCOCC=2)=CN2C1=NC=C2C(C=C1F)=CC=C1C(=O)NC1CC1 BUMVFGYLRJBZDM-UHFFFAOYSA-N 0.000 claims 1
• UBEOIMNFBZNDEP-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-[(4-hydroxy-3-methylbutyl)amino]imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound C=1N=C2C(NCCC(CO)C)=NC(C=3CCOCC=3)=CN2C=1C(C=C1C)=CC=C1C(=O)NC1CC1 UBEOIMNFBZNDEP-UHFFFAOYSA-N 0.000 claims 1
• HFGBDDNUDCCKNR-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-[(4-hydroxy-4-methylcyclohexyl)methylamino]imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=C(N=C(NCC4CCC(C)(O)CC4)C3=NC=2)C=2CCOCC=2)=CC=C1C(=O)NC1CC1 HFGBDDNUDCCKNR-UHFFFAOYSA-N 0.000 claims 1
• SOXJDQWVKYUUCV-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-[(4-methylmorpholin-2-yl)methylamino]imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound C1N(C)CCOC1CNC1=NC(C=2CCOCC=2)=CN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 SOXJDQWVKYUUCV-UHFFFAOYSA-N 0.000 claims 1
• LNXVTRZTBQOZCO-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-[(5-oxopyrrolidin-3-yl)methylamino]imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=C(N=C(NCC4CC(=O)NC4)C3=NC=2)C=2CCOCC=2)=CC=C1C(=O)NC1CC1 LNXVTRZTBQOZCO-UHFFFAOYSA-N 0.000 claims 1
• LHIRWOFYRBKQGU-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-[2-(1-methylpiperidin-4-yl)ethylamino]imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound C1CN(C)CCC1CCNC1=NC(C=2CCOCC=2)=CN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 LHIRWOFYRBKQGU-UHFFFAOYSA-N 0.000 claims 1
• XFTQFRUUFHIANC-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-pyran-4-yl)-8-[[4-(dimethylamino)cyclohexyl]methylamino]imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound C1CC(N(C)C)CCC1CNC1=NC(C=2CCOCC=2)=CN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 XFTQFRUUFHIANC-UHFFFAOYSA-N 0.000 claims 1
• ISGJRWQDEXXGRI-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,6-dihydro-2h-thiopyran-4-yl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=C(N=C(NCCC(F)(F)F)C3=NC=2)C=2CCSCC=2)=CC=C1C(=O)NC1CC1 ISGJRWQDEXXGRI-UHFFFAOYSA-N 0.000 claims 1
• ASMGPQXQJFTGBY-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=C(OC=4C=C(F)C=CC=4)N=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 ASMGPQXQJFTGBY-UHFFFAOYSA-N 0.000 claims 1
• ZKZXUFVEINKYQD-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=C(OC=4C=C(F)C=CC=4)N=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 ZKZXUFVEINKYQD-UHFFFAOYSA-N 0.000 claims 1
• YIVPKAAULRBPEY-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenyl)sulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=C(SC=4C=C(F)C=CC=4)N=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 YIVPKAAULRBPEY-UHFFFAOYSA-N 0.000 claims 1
• QGVZMVFNNSCAPW-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-hydroxy-3-methylbutyl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(CCC(C)(C)O)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 QGVZMVFNNSCAPW-UHFFFAOYSA-N 0.000 claims 1
• NMWVVFCEORONNF-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-fluoropyridin-3-yl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3C=C(F)C=NC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 NMWVVFCEORONNF-UHFFFAOYSA-N 0.000 claims 1
• GXOMLADROMYFGF-UHFFFAOYSA-N n-cyclopropyl-4-[6-(6-ethoxypyridin-3-yl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]-2-methylbenzamide Chemical compound C1=NC(OCC)=CC=C1C(N=C1NCCC(F)(F)F)=CN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 GXOMLADROMYFGF-UHFFFAOYSA-N 0.000 claims 1
• JBTGDYRTSIEERD-UHFFFAOYSA-N n-cyclopropyl-4-[6-(6-fluoropyridin-3-yl)-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3C=NC(F)=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 JBTGDYRTSIEERD-UHFFFAOYSA-N 0.000 claims 1
• IHVKOTGNAVMLHV-UHFFFAOYSA-N n-cyclopropyl-4-[6-[3-(dimethylamino)propyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(CCCN(C)C)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 IHVKOTGNAVMLHV-UHFFFAOYSA-N 0.000 claims 1
• XPQORUGYJABSBI-UHFFFAOYSA-N n-cyclopropyl-4-[6-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C=3C=CC(=CC=3)C=3OC(C)=NN=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 XPQORUGYJABSBI-UHFFFAOYSA-N 0.000 claims 1
• SRICOVSOEKYPSM-UHFFFAOYSA-N n-cyclopropyl-4-[6-imidazo[1,2-a]pyridin-6-yl-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC(C3=CN4C=CN=C4C=C3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 SRICOVSOEKYPSM-UHFFFAOYSA-N 0.000 claims 1
• WNKQKPCBCLAVBH-UHFFFAOYSA-N n-cyclopropyl-4-[6-pyridin-4-yl-8-(2-sulfamoylethylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCCS(=O)(=O)N)=NC(C=3C=CN=CC=3)=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 WNKQKPCBCLAVBH-UHFFFAOYSA-N 0.000 claims 1
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