CA2821829A1 - Imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders - Google Patents

Info

Publication number

CA2821829A1

CA2821829A1 CA2821829A CA2821829A CA2821829A1 CA 2821829 A1 CA2821829 A1 CA 2821829A1 CA 2821829 A CA2821829 A CA 2821829A CA 2821829 A CA2821829 A CA 2821829A CA 2821829 A1 CA2821829 A1 CA 2821829A1

Authority

CA

Canada

Prior art keywords

pyrazin

imidazo

cyclopropyl

amino

alkyl

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 35
• 230000003463 hyperproliferative effect Effects 0.000 title abstract description 7
• 150000005235 imidazopyrazines Chemical class 0.000 title abstract description 4
• 239000003112 inhibitor Substances 0.000 title description 15
• 150000001875 compounds Chemical class 0.000 claims abstract description 230
• 238000000034 method Methods 0.000 claims abstract description 60
• 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
• -1 or a HO- Chemical group 0.000 claims description 285
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 190
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 112
• 239000000203 mixture Substances 0.000 claims description 89
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 75
• 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 74
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 69
• 206010028980 Neoplasm Diseases 0.000 claims description 68
• 150000003839 salts Chemical class 0.000 claims description 53
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
• 238000002360 preparation method Methods 0.000 claims description 46
• 125000001072 heteroaryl group Chemical group 0.000 claims description 38
• 125000005843 halogen group Chemical group 0.000 claims description 34
• 125000003118 aryl group Chemical group 0.000 claims description 31
• 239000001257 hydrogen Substances 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
• 239000012453 solvate Substances 0.000 claims description 26
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• 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 19
• 239000003814 drug Substances 0.000 claims description 19
• 150000002148 esters Chemical class 0.000 claims description 19
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
• 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
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
• 125000005418 aryl aryl group Chemical group 0.000 claims description 13
• 239000000460 chlorine Substances 0.000 claims description 12
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 11
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
• 102100036109 Dual specificity protein kinase TTK Human genes 0.000 claims description 8
• 101000659223 Homo sapiens Dual specificity protein kinase TTK Proteins 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 208000032839 leukemia Diseases 0.000 claims description 8
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
• 206010025323 Lymphomas Diseases 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• 229910052740 iodine Inorganic materials 0.000 claims description 7
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-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
• 125000000524 functional group Chemical group 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
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 5
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
• 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
• 210000000038 chest Anatomy 0.000 claims description 5
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 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
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
• 125000005620 boronic acid group Chemical class 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• 229910052736 halogen Inorganic materials 0.000 claims description 3
• 150000002367 halogens Chemical class 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims description 3
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 229960000581 salicylamide Drugs 0.000 claims description 3
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 2
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 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
• GBJJEOMGAISHBT-UHFFFAOYSA-N n-cyclopropyl-4-[8-(pentylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCCCCC)=NC=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 GBJJEOMGAISHBT-UHFFFAOYSA-N 0.000 claims description 2
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 2
• YUHKXKGPLTYXSO-UHFFFAOYSA-N n-cyclopropyl-4-[8-(thiophen-2-ylmethylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1C=C(C=2N3C=CN=C(NCC=4SC=CC=4)C3=NC=2)C=CC=1C(=O)NC1CC1 YUHKXKGPLTYXSO-UHFFFAOYSA-N 0.000 claims 2
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
• WPPHQBOIDPPQRF-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)(O)C)=NC=CN2C=1C(C=C1Cl)=CC=C1C(=O)NC1CC1 WPPHQBOIDPPQRF-UHFFFAOYSA-N 0.000 claims 1
• MCGKKBSOGWKPMH-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[8-[(3,3,3-trifluoro-2-hydroxypropyl)amino]imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(O)C(F)(F)F)=NC=CN2C=1C(C=C1Cl)=CC=C1C(=O)NC1CC1 MCGKKBSOGWKPMH-UHFFFAOYSA-N 0.000 claims 1
• 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
• 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims 1
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
• 125000000981 3-amino-3-oxopropyl group Chemical group [H]C([*])([H])C([H])([H])C(=O)N([H])[H] 0.000 claims 1
• 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims 1
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
• NBAXGQMDAKCKIW-UHFFFAOYSA-N 4-[5-bromo-8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=NC=C(Br)N2C=1C(C=C1)=CC=C1C(=O)NC1CC1 NBAXGQMDAKCKIW-UHFFFAOYSA-N 0.000 claims 1
• YGQYWYACPCYMPJ-UHFFFAOYSA-N 4-[8-(benzylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3C=CN=C(NCC=4C=CC=CC=4)C3=NC=2)=CC=C1C(=O)NC1CC1 YGQYWYACPCYMPJ-UHFFFAOYSA-N 0.000 claims 1
• TWYNALZSINMBCM-UHFFFAOYSA-N 4-[8-(butylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound C=1N=C2C(NCCCC)=NC=CN2C=1C(C=C1C)=CC=C1C(=O)NC1CC1 TWYNALZSINMBCM-UHFFFAOYSA-N 0.000 claims 1
• SKRFUWYONYPJMR-UHFFFAOYSA-N 4-[8-(butylamino)imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCCCC)=NC=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 SKRFUWYONYPJMR-UHFFFAOYSA-N 0.000 claims 1
• UPIPQGKFJKHWPH-UHFFFAOYSA-N 4-[8-[(3-amino-3-oxopropyl)amino]imidazo[1,2-a]pyrazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCCC(=O)N)=NC=CN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 UPIPQGKFJKHWPH-UHFFFAOYSA-N 0.000 claims 1
• SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims 1
• 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 1
• OJLKYTQRGWLWSB-UHFFFAOYSA-N C(C1=CC=CC=C1)NC=1C=2N(C=CN1)C(=CN2)C2=CC(=C(C(=O)NC1CC1)C=C2)Cl.ClC2=C(C(=O)NC1CC1)C=CC(=C2)C2=CN=C1N2C=CN=C1NCCCCO Chemical compound C(C1=CC=CC=C1)NC=1C=2N(C=CN1)C(=CN2)C2=CC(=C(C(=O)NC1CC1)C=C2)Cl.ClC2=C(C(=O)NC1CC1)C=CC(=C2)C2=CN=C1N2C=CN=C1NCCCCO OJLKYTQRGWLWSB-UHFFFAOYSA-N 0.000 claims 1
• XFEGELKLHIZSKW-UHFFFAOYSA-N C(CCC)NC=1C=2N(C=CN1)C(=CN2)C2=CC(=C(C(=O)NC1CC1)C=C2)Cl.ClC2=C(C(=O)NC1CC1)C=CC(=C2)C2=CN=C1N2C=CN=C1NCCCO Chemical compound C(CCC)NC=1C=2N(C=CN1)C(=CN2)C2=CC(=C(C(=O)NC1CC1)C=C2)Cl.ClC2=C(C(=O)NC1CC1)C=CC(=C2)C2=CN=C1N2C=CN=C1NCCCO XFEGELKLHIZSKW-UHFFFAOYSA-N 0.000 claims 1
• ZANVPFPCKDLRKI-UHFFFAOYSA-N C1(CC1)NC(C1=C(C=C(C=C1)C1=CN=C2N1C=CN=C2NCC(C)OCC)O)=O.C2(CC2)NC(C2=C(C=C(C=C2)C2=CN=C1N2C=CN=C1NCC=1C=NN(C1)C)O)=O Chemical compound C1(CC1)NC(C1=C(C=C(C=C1)C1=CN=C2N1C=CN=C2NCC(C)OCC)O)=O.C2(CC2)NC(C2=C(C=C(C=C2)C2=CN=C1N2C=CN=C1NCC=1C=NN(C1)C)O)=O ZANVPFPCKDLRKI-UHFFFAOYSA-N 0.000 claims 1
• MARQUOZLVAVJIB-UHFFFAOYSA-N C1(CC1)NC(C1=CC=C(C=C1)C1=CN=C2N1C=CN=C2NCC2=CC(=C(C(=C2)OC)OC)OC)=O.C(C2=CC=CC=C2)NC=2C=1N(C=CN2)C(=CN1)C1=CC=C(C(=O)NC2CC2)C=C1 Chemical compound C1(CC1)NC(C1=CC=C(C=C1)C1=CN=C2N1C=CN=C2NCC2=CC(=C(C(=C2)OC)OC)OC)=O.C(C2=CC=CC=C2)NC=2C=1N(C=CN2)C(=CN1)C1=CC=C(C(=O)NC2CC2)C=C1 MARQUOZLVAVJIB-UHFFFAOYSA-N 0.000 claims 1
• PTSCTAZKRDCDLB-UHFFFAOYSA-N ClC1=C(C(=O)NC2CC2)C=CC(=C1)C1=CN=C2N1C=CN=C2NCC2=CC=C(C=C2)F.ClC2=C(C(=O)NC1CC1)C=CC(=C2)C2=CN=C1N2C=CN=C1NCC1=C(C=CC=C1)F Chemical compound ClC1=C(C(=O)NC2CC2)C=CC(=C1)C1=CN=C2N1C=CN=C2NCC2=CC=C(C=C2)F.ClC2=C(C(=O)NC1CC1)C=CC(=C2)C2=CN=C1N2C=CN=C1NCC1=C(C=CC=C1)F PTSCTAZKRDCDLB-UHFFFAOYSA-N 0.000 claims 1
• GRAGNKUDMCGWFC-UHFFFAOYSA-N ClC1=C(C(=O)NC2CC2)C=CC(=C1)C1=CN=C2N1C=CN=C2NCC2OCCC2.ClC2=C(C(=O)NC1CC1)C=CC(=C2)C2=CN=C1N2C=CN=C1NCC1=CC(=CC=C1)F Chemical compound ClC1=C(C(=O)NC2CC2)C=CC(=C1)C1=CN=C2N1C=CN=C2NCC2OCCC2.ClC2=C(C(=O)NC1CC1)C=CC(=C2)C2=CN=C1N2C=CN=C1NCC1=CC(=CC=C1)F GRAGNKUDMCGWFC-UHFFFAOYSA-N 0.000 claims 1
• FONVXZKVIFWHLP-UHFFFAOYSA-N ClC1=C(C(=O)NC2CC2)C=CC(=C1)C1=CN=C2N1C=CN=C2NCCOC.ClC2=C(C(=O)NC1CC1)C=CC(=C2)C2=CN=C1N2C=CN=C1NCCCN1C(CCC1)=O Chemical compound ClC1=C(C(=O)NC2CC2)C=CC(=C1)C1=CN=C2N1C=CN=C2NCCOC.ClC2=C(C(=O)NC1CC1)C=CC(=C2)C2=CN=C1N2C=CN=C1NCCCN1C(CCC1)=O FONVXZKVIFWHLP-UHFFFAOYSA-N 0.000 claims 1
• VAJRJUSLKFCCKN-UHFFFAOYSA-N N-cyclopropyl-2-hydroxy-4-[8-(2-hydroxypropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide N-cyclopropyl-2-hydroxy-4-[8-(3,3,3-trifluoropropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C1(CC1)NC(C1=C(C=C(C=C1)C1=CN=C2N1C=CN=C2NCC(C)O)O)=O.C2(CC2)NC(C2=C(C=C(C=C2)C2=CN=C1N2C=CN=C1NCCC(F)(F)F)O)=O VAJRJUSLKFCCKN-UHFFFAOYSA-N 0.000 claims 1
• LQUUGUIBQSDRIF-UHFFFAOYSA-N NCCCNC=1C=2N(C=CN1)C(=CN2)C2=C(C=C(C(=O)NC1CC1)C=C2)OC.NCCCNC=2C=1N(C=CN2)C(=CN1)C1=CC(=C(C(=O)NC2CC2)C=C1)Cl Chemical compound NCCCNC=1C=2N(C=CN1)C(=CN2)C2=C(C=C(C(=O)NC1CC1)C=C2)OC.NCCCNC=2C=1N(C=CN2)C(=CN1)C1=CC(=C(C(=O)NC2CC2)C=C1)Cl LQUUGUIBQSDRIF-UHFFFAOYSA-N 0.000 claims 1
• 150000001721 carbon Chemical group 0.000 claims 1
• PLWPBMVJMJUVBZ-UHFFFAOYSA-N n-cyclopropyl-2-hydroxy-4-[8-(oxolan-2-ylmethylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound OC1=CC(C=2N3C=CN=C(NCC4OCCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 PLWPBMVJMJUVBZ-UHFFFAOYSA-N 0.000 claims 1
• RZOSGONDPNDPKL-UHFFFAOYSA-N n-cyclopropyl-2-hydroxy-4-[8-(propylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCCC)=NC=CN2C=1C(C=C1O)=CC=C1C(=O)NC1CC1 RZOSGONDPNDPKL-UHFFFAOYSA-N 0.000 claims 1
• QDWLCUDSRVRLFF-UHFFFAOYSA-N n-cyclopropyl-2-hydroxy-4-[8-(thiophen-2-ylmethylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound OC1=CC(C=2N3C=CN=C(NCC=4SC=CC=4)C3=NC=2)=CC=C1C(=O)NC1CC1 QDWLCUDSRVRLFF-UHFFFAOYSA-N 0.000 claims 1
• LSRFSAKUBIHKCC-UHFFFAOYSA-N n-cyclopropyl-2-hydroxy-4-[8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)(O)C)=NC=CN2C=1C(C=C1O)=CC=C1C(=O)NC1CC1 LSRFSAKUBIHKCC-UHFFFAOYSA-N 0.000 claims 1
• FCLYKQGCTKSYSA-UHFFFAOYSA-N n-cyclopropyl-2-hydroxy-4-[8-[(3,3,3-trifluoro-2-hydroxypropyl)amino]imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(O)C(F)(F)F)=NC=CN2C=1C(C=C1O)=CC=C1C(=O)NC1CC1 FCLYKQGCTKSYSA-UHFFFAOYSA-N 0.000 claims 1
• DLCRZBSBOCYDKN-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[8-(3-methylsulfonylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3C=CN=C(NCCCS(C)(=O)=O)C3=NC=2)=CC=C1C(=O)NC1CC1 DLCRZBSBOCYDKN-UHFFFAOYSA-N 0.000 claims 1
• BRDBVOFIPPNPFN-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[8-[(3,3,3-trifluoro-2-hydroxypropyl)amino]imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3C=CN=C(NCC(O)C(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 BRDBVOFIPPNPFN-UHFFFAOYSA-N 0.000 claims 1
• HTGGHQYEKUPNFG-UHFFFAOYSA-N n-cyclopropyl-3-methoxy-4-[8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1C=C(C=2N3C=CN=C(NCC(C)C)C3=NC=2)C(OC)=CC=1C(=O)NC1CC1 HTGGHQYEKUPNFG-UHFFFAOYSA-N 0.000 claims 1
• ROKREJRMVRGYEL-UHFFFAOYSA-N n-cyclopropyl-3-methyl-4-[8-(2-methylpropylamino)imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=NC=CN2C=1C(C(=C1)C)=CC=C1C(=O)NC1CC1 ROKREJRMVRGYEL-UHFFFAOYSA-N 0.000 claims 1
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