WO2009102468A1 - 6-aryl-imidaz0[l, 2-a] pyrazine derivatives, method of making, and method of use thereof - Google Patents
6-aryl-imidaz0[l, 2-a] pyrazine derivatives, method of making, and method of use thereof Download PDFInfo
- Publication number
- WO2009102468A1 WO2009102468A1 PCT/US2009/000919 US2009000919W WO2009102468A1 WO 2009102468 A1 WO2009102468 A1 WO 2009102468A1 US 2009000919 W US2009000919 W US 2009000919W WO 2009102468 A1 WO2009102468 A1 WO 2009102468A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- pyrazin
- optionally substituted
- imidazo
- amino
- phenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 61
- 238000004519 manufacturing process Methods 0.000 title description 5
- GXWNSJYVSIJRLS-UHFFFAOYSA-N 6-bromo-8-methylimidazo[1,2-a]pyrazine Chemical class CC1=NC(Br)=CN2C=CN=C12 GXWNSJYVSIJRLS-UHFFFAOYSA-N 0.000 title 1
- 150000005829 chemical entities Chemical class 0.000 claims abstract description 119
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 230000000694 effects Effects 0.000 claims abstract description 61
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 52
- 201000010099 disease Diseases 0.000 claims abstract description 34
- 230000005764 inhibitory process Effects 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 19
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
- 208000010668 atopic eczema Diseases 0.000 claims abstract description 19
- 208000035475 disorder Diseases 0.000 claims abstract description 18
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 18
- 230000000172 allergic effect Effects 0.000 claims abstract description 17
- 201000011510 cancer Diseases 0.000 claims abstract description 17
- 206010061218 Inflammation Diseases 0.000 claims abstract description 12
- 230000001154 acute effect Effects 0.000 claims abstract description 12
- 230000004054 inflammatory process Effects 0.000 claims abstract description 12
- 208000003950 B-cell lymphoma Diseases 0.000 claims abstract description 4
- 208000004736 B-Cell Leukemia Diseases 0.000 claims abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 214
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 136
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 119
- -1 amino, carboxy Chemical group 0.000 claims description 114
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 102
- 229910052739 hydrogen Inorganic materials 0.000 claims description 101
- 239000001257 hydrogen Substances 0.000 claims description 101
- 125000001072 heteroaryl group Chemical group 0.000 claims description 98
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 71
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 61
- 150000002431 hydrogen Chemical class 0.000 claims description 56
- 125000003107 substituted aryl group Chemical group 0.000 claims description 56
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 53
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 53
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 48
- 210000003719 b-lymphocyte Anatomy 0.000 claims description 44
- 210000004027 cell Anatomy 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000003368 amide group Chemical group 0.000 claims description 20
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 20
- 239000005711 Benzoic acid Substances 0.000 claims description 19
- 235000010233 benzoic acid Nutrition 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 15
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 15
- 229910052727 yttrium Inorganic materials 0.000 claims description 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 208000006673 asthma Diseases 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 238000000338 in vitro Methods 0.000 claims description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 6
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 238000001514 detection method Methods 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 5
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 5
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 4
- 206010020751 Hypersensitivity Diseases 0.000 claims description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 4
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 4
- 208000026935 allergic disease Diseases 0.000 claims description 4
- 201000010105 allergic rhinitis Diseases 0.000 claims description 4
- NLTWIBYLUOZHMI-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-6-phenylimidazo[1,2-a]pyrazin-8-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=CC=CC=2)=CN2C1=NC=C2 NLTWIBYLUOZHMI-UHFFFAOYSA-N 0.000 claims description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 230000007815 allergy Effects 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 235000005152 nicotinamide Nutrition 0.000 claims description 3
- 239000011570 nicotinamide Substances 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- RKMUNAWTRSQGOI-UHFFFAOYSA-N 1,4-diazepan-1-yl-[4-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]phenyl]methanone Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=CC(=CC=2)C(=O)N2CCNCCC2)=CN2C1=NC=C2 RKMUNAWTRSQGOI-UHFFFAOYSA-N 0.000 claims description 2
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- URPMFNXQRORTOR-UHFFFAOYSA-N 3-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-5-methylbenzamide Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C(C=C(C)C=2)C(N)=O)=CN2C1=NC=C2 URPMFNXQRORTOR-UHFFFAOYSA-N 0.000 claims description 2
- ZZKLDJKQVHFVMF-UHFFFAOYSA-N 3-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C(C=CC=2)C(=O)NC2CCN(C)CC2)=CN2C1=NC=C2 ZZKLDJKQVHFVMF-UHFFFAOYSA-N 0.000 claims description 2
- LINWWBDERPBFPJ-UHFFFAOYSA-N 3-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(C=2N=C(NC=3C=C(OC)C(OC)=CC=3)C3=NC=CN3C=2)=C1 LINWWBDERPBFPJ-UHFFFAOYSA-N 0.000 claims description 2
- JTTWRYKSIWBEAS-UHFFFAOYSA-N 3-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-n-[4-(1h-1,2,4-triazol-5-yl)phenyl]benzamide Chemical compound C=1C=CC(C=2N=C(NC=3C=CC(=CC=3)N3CCOCC3)C3=NC=CN3C=2)=CC=1C(=O)NC(C=C1)=CC=C1C=1N=CNN=1 JTTWRYKSIWBEAS-UHFFFAOYSA-N 0.000 claims description 2
- YJIQOKBKQQSKTA-UHFFFAOYSA-N 3-[8-[4-(4-ethylpiperazin-1-yl)anilino]imidazo[1,2-a]pyrazin-6-yl]-n-[4-(methylcarbamoyl)phenyl]benzamide Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C(C=CC=2)C(=O)NC=2C=CC(=CC=2)C(=O)NC)=CN2C1=NC=C2 YJIQOKBKQQSKTA-UHFFFAOYSA-N 0.000 claims description 2
- OMQFQYBXJFOJGI-UHFFFAOYSA-N 4-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-2-methoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C(OC)C(C(N)=O)=CC=2)=CN2C1=NC=C2 OMQFQYBXJFOJGI-UHFFFAOYSA-N 0.000 claims description 2
- FFQQZNPVCLRHSO-UHFFFAOYSA-N 4-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-3-fluorobenzamide Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C(=CC(=CC=2)C(N)=O)F)=CN2C1=NC=C2 FFQQZNPVCLRHSO-UHFFFAOYSA-N 0.000 claims description 2
- FVGGBGMRQARQSR-UHFFFAOYSA-N 4-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-n-(2-hydroxyethyl)benzamide Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=CC(=CC=2)C(=O)NCCO)=CN2C1=NC=C2 FVGGBGMRQARQSR-UHFFFAOYSA-N 0.000 claims description 2
- LDXOCJGKJKOVCI-UHFFFAOYSA-N 4-[8-(3-methoxy-4-piperidin-4-yloxyanilino)imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C=1C=C(OC2CCNCC2)C(OC)=CC=1NC(C1=NC=CN1C=1)=NC=1C1=CC=C(C(N)=O)C=C1 LDXOCJGKJKOVCI-UHFFFAOYSA-N 0.000 claims description 2
- OYCXXZSLIOIJKR-UHFFFAOYSA-N 4-[8-[3-methoxy-4-(1h-pyrazol-5-yl)anilino]imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C=1C=C(C=2NN=CC=2)C(OC)=CC=1NC(C1=NC=CN1C=1)=NC=1C1=CC=C(C(N)=O)C=C1 OYCXXZSLIOIJKR-UHFFFAOYSA-N 0.000 claims description 2
- WYORQKLWLSWCLP-UHFFFAOYSA-N 4-[8-[3-methoxy-4-(2-methoxyethoxy)anilino]imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C1=C(OC)C(OCCOC)=CC=C1NC1=NC(C=2C=CC(=CC=2)C(N)=O)=CN2C1=NC=C2 WYORQKLWLSWCLP-UHFFFAOYSA-N 0.000 claims description 2
- DLURKCMHCJHLIP-UHFFFAOYSA-N 4-[8-[4-(2-hydroxyethoxy)-3-methoxyanilino]imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C1=C(OCCO)C(OC)=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=CC(=CC=2)C(N)=O)=C1 DLURKCMHCJHLIP-UHFFFAOYSA-N 0.000 claims description 2
- GRDRGPRTIPDDMO-UHFFFAOYSA-N 4-[8-[4-(2-hydroxypropan-2-yl)anilino]imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1NC1=NC(C=2C=CC(=CC=2)C(N)=O)=CN2C1=NC=C2 GRDRGPRTIPDDMO-UHFFFAOYSA-N 0.000 claims description 2
- IJRVYAFTPOEYGC-UHFFFAOYSA-N 4-[8-[4-(cyanomethoxy)-3-methoxyanilino]imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C1=C(OCC#N)C(OC)=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=CC(=CC=2)C(N)=O)=C1 IJRVYAFTPOEYGC-UHFFFAOYSA-N 0.000 claims description 2
- ZNOVQLVNHUAXJR-UHFFFAOYSA-N 4-[8-[4-(propylcarbamoyl)anilino]imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C1=CC(C(=O)NCCC)=CC=C1NC1=NC(C=2C=CC(=CC=2)C(N)=O)=CN2C1=NC=C2 ZNOVQLVNHUAXJR-UHFFFAOYSA-N 0.000 claims description 2
- MIASYBOTPYONAA-UHFFFAOYSA-N 5-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-2-fluorobenzamide Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C(C(F)=CC=2)C(N)=O)=CN2C1=NC=C2 MIASYBOTPYONAA-UHFFFAOYSA-N 0.000 claims description 2
- OXXRNHFLDDEUHI-UHFFFAOYSA-N 5-[8-(4-ethoxy-3-methoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-2-methyl-n-[4-(methylcarbamoyl)phenyl]benzamide Chemical compound C1=C(OC)C(OCC)=CC=C1NC1=NC(C=2C=C(C(C)=CC=2)C(=O)NC=2C=CC(=CC=2)C(=O)NC)=CN2C1=NC=C2 OXXRNHFLDDEUHI-UHFFFAOYSA-N 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- AKXYESPWTFMHHC-UHFFFAOYSA-N N-[4-(hydroxycarbamoyl)phenyl]-3-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1NC(=O)C1=CC=CC(C=2N=C(NC=3C=CC(=CC=3)N3CCOCC3)C3=NC=CN3C=2)=C1 AKXYESPWTFMHHC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000005959 diazepanyl group Chemical group 0.000 claims description 2
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- UGWOVXJSXCMZBU-UHFFFAOYSA-N n-[4-(methylaminomethyl)phenyl]-3-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C1=CC(CNC)=CC=C1NC(=O)C1=CC=CC(C=2N=C(NC=3C=CC(=CC=3)N3CCOCC3)C3=NC=CN3C=2)=C1 UGWOVXJSXCMZBU-UHFFFAOYSA-N 0.000 claims description 2
- DTRNBNABTXHZRD-UHFFFAOYSA-N n-[4-(methylcarbamoyl)phenyl]-3-[8-[4-(3-oxopiperazin-1-yl)anilino]imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C1=CC(C(=O)NC)=CC=C1NC(=O)C1=CC=CC(C=2N=C(NC=3C=CC(=CC=3)N3CC(=O)NCC3)C3=NC=CN3C=2)=C1 DTRNBNABTXHZRD-UHFFFAOYSA-N 0.000 claims description 2
- VOIUTIDSXYTWSF-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]phenyl]-3-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C1=CC(CN(C)C)=CC=C1NC(=O)C1=CC=CC(C=2N=C(NC=3C=CC(=CC=3)N3CCOCC3)C3=NC=CN3C=2)=C1 VOIUTIDSXYTWSF-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 8
- RUEXXBLPQRAHKO-UHFFFAOYSA-N 1,4-diazepan-1-yl-[3-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]phenyl]methanone Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C(C=CC=2)C(=O)N2CCNCCC2)=CN2C1=NC=C2 RUEXXBLPQRAHKO-UHFFFAOYSA-N 0.000 claims 1
- SVEZKRNALWDRDS-UHFFFAOYSA-N 2,3-dihydroindol-1-yl-[3-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]phenyl]methanone Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C(C=CC=2)C(=O)N2C3=CC=CC=C3CC2)=CN2C1=NC=C2 SVEZKRNALWDRDS-UHFFFAOYSA-N 0.000 claims 1
- FXTYUBNNUMLKFI-UHFFFAOYSA-N 2-[4-(1H-pyrazol-4-yl)phenyl]benzamide Chemical compound N1N=CC(=C1)C1=CC=C(C=C1)C1=C(C(=O)N)C=CC=C1 FXTYUBNNUMLKFI-UHFFFAOYSA-N 0.000 claims 1
- LITWNIJIWANOEQ-UHFFFAOYSA-N 2-[4-[3-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]benzoyl]piperazin-1-yl]acetic acid Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C(C=CC=2)C(=O)N2CCN(CC(O)=O)CC2)=CN2C1=NC=C2 LITWNIJIWANOEQ-UHFFFAOYSA-N 0.000 claims 1
- JJIMFDVLZIUDKF-UHFFFAOYSA-N 3,4-dihydro-1h-isoquinolin-2-yl-[3-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]phenyl]methanone Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C(C=CC=2)C(=O)N2CC3=CC=CC=C3CC2)=CN2C1=NC=C2 JJIMFDVLZIUDKF-UHFFFAOYSA-N 0.000 claims 1
- YHDIZZXGYRPSOY-UHFFFAOYSA-N 3-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-5-fluorobenzamide Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C(C=C(F)C=2)C(N)=O)=CN2C1=NC=C2 YHDIZZXGYRPSOY-UHFFFAOYSA-N 0.000 claims 1
- IYOSBXIROJTSLT-UHFFFAOYSA-N 3-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-n-[4-(1-hydroxyethyl)phenyl]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C(C=CC=2)C(=O)NC=2C=CC(=CC=2)C(C)O)=CN2C1=NC=C2 IYOSBXIROJTSLT-UHFFFAOYSA-N 0.000 claims 1
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Abstract
Description
Claims
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CA2714414A CA2714414A1 (en) | 2008-02-13 | 2009-02-12 | Certain substituted amides, method of making, and method of use thereof |
EP09710901A EP2252617A1 (en) | 2008-02-13 | 2009-02-12 | 6-aryl-imidaz0[l, 2-a]pyrazine derivatives, method of making, and method of use thereof |
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JP2010546786A JP5496915B2 (en) | 2008-02-13 | 2009-02-12 | 6-Aryl-imidazo [1,2-a] pyrazine derivatives, methods for their preparation, and methods for their use |
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CA2714414A1 (en) | 2009-08-20 |
JP2011511835A (en) | 2011-04-14 |
EP2252617A1 (en) | 2010-11-24 |
US20130023499A1 (en) | 2013-01-24 |
US20090221612A1 (en) | 2009-09-03 |
AU2009215191A1 (en) | 2009-08-20 |
US8697699B2 (en) | 2014-04-15 |
NZ587039A (en) | 2013-01-25 |
JP5496915B2 (en) | 2014-05-21 |
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