AU2003270318B2 - Imidazolopyridines and methods of making and using the same - Google Patents

Info

Publication number

AU2003270318B2

AU2003270318B2 AU2003270318A AU2003270318A AU2003270318B2 AU 2003270318 B2 AU2003270318 B2 AU 2003270318B2 AU 2003270318 A AU2003270318 A AU 2003270318A AU 2003270318 A AU2003270318 A AU 2003270318A AU 2003270318 B2 AU2003270318 B2 AU 2003270318B2

Authority

AU

Australia

Prior art keywords

pyridin

methyl

pyrimidin

imidazo

amino

Prior art date

2002-09-06

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
• Discuss

• 238000000034 method Methods 0.000 title claims description 38
• GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 title 1
• 125000000217 alkyl group Chemical group 0.000 claims description 188
• -1 hydroxy, amino Chemical group 0.000 claims description 162
• 150000001875 compounds Chemical class 0.000 claims description 141
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 118
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 108
• 125000001072 heteroaryl group Chemical group 0.000 claims description 85
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 76
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 65
• 125000003545 alkoxy group Chemical group 0.000 claims description 54
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 44
• 125000004414 alkyl thio group Chemical group 0.000 claims description 44
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 43
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 40
• 125000003118 aryl group Chemical group 0.000 claims description 37
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 37
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
• 125000002252 acyl group Chemical group 0.000 claims description 32
• 210000004027 cell Anatomy 0.000 claims description 32
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
• 125000005843 halogen group Chemical group 0.000 claims description 31
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 28
• QAALUNOPVWULBE-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxylic acid Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(O)=O)C=2N=C(N)N=CC=2)=N1 QAALUNOPVWULBE-UHFFFAOYSA-N 0.000 claims description 24
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 24
• 239000002253 acid Substances 0.000 claims description 23
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
• 125000003342 alkenyl group Chemical group 0.000 claims description 22
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 22
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 20
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 20
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 20
• DRUPRNRFTAHFGT-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)S(C)(=O)=O)=N1 DRUPRNRFTAHFGT-UHFFFAOYSA-N 0.000 claims description 19
• 125000000304 alkynyl group Chemical group 0.000 claims description 19
• NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 19
• 206010028980 Neoplasm Diseases 0.000 claims description 18
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 18
• 125000004104 aryloxy group Chemical group 0.000 claims description 18
• 208000035475 disorder Diseases 0.000 claims description 18
• 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 18
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 18
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 16
• 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 16
• 125000001188 haloalkyl group Chemical group 0.000 claims description 16
• 125000003435 aroyl group Chemical group 0.000 claims description 15
• 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims description 15
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 15
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 15
• KLLKKKAXFTYAGU-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxylic acid Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C(O)=O)C=2N=C(N)N=CC=2)=N1 KLLKKKAXFTYAGU-UHFFFAOYSA-N 0.000 claims description 14
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 14
• 206010016654 Fibrosis Diseases 0.000 claims description 14
• 201000010099 disease Diseases 0.000 claims description 14
• 230000003176 fibrotic effect Effects 0.000 claims description 14
• 230000004761 fibrosis Effects 0.000 claims description 13
• PREOONMJIVUPMI-UHFFFAOYSA-N 1,4-dioxan-2-ylmethanamine Chemical compound NCC1COCCO1 PREOONMJIVUPMI-UHFFFAOYSA-N 0.000 claims description 12
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 12
• 150000001412 amines Chemical class 0.000 claims description 12
• 239000004202 carbamide Substances 0.000 claims description 12
• 230000019491 signal transduction Effects 0.000 claims description 12
• 102000010834 Extracellular Matrix Proteins Human genes 0.000 claims description 11
• 108010037362 Extracellular Matrix Proteins Proteins 0.000 claims description 11
• 150000001408 amides Chemical class 0.000 claims description 11
• 125000004122 cyclic group Chemical group 0.000 claims description 11
• 210000002744 extracellular matrix Anatomy 0.000 claims description 11
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 11
• 230000002401 inhibitory effect Effects 0.000 claims description 11
• 229940080818 propionamide Drugs 0.000 claims description 11
• 239000001257 hydrogen Substances 0.000 claims description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims description 10
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 10
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 9
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 9
• 125000005163 aryl sulfanyl group Chemical group 0.000 claims description 9
• 125000005171 cycloalkylsulfanyl group Chemical group 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical compound NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 claims description 8
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 8
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 8
• HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 claims description 8
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 8
• 239000011570 nicotinamide Substances 0.000 claims description 8
• 229960003966 nicotinamide Drugs 0.000 claims description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
• 230000037390 scarring Effects 0.000 claims description 8
• VYFQAELHCIQANB-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound CSC1=NC=CC(C=2N3C=CC(N)=NC3=NC=2C=2N=C(C)C=CC=2)=N1 VYFQAELHCIQANB-UHFFFAOYSA-N 0.000 claims description 7
• JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 7
• WHIRSMPBKKWVNL-UHFFFAOYSA-N 6-[8-bromo-6-methyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-1h-pyrimidin-2-one Chemical compound N12C=C(C)C=C(Br)C2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(O)=N1 WHIRSMPBKKWVNL-UHFFFAOYSA-N 0.000 claims description 7
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 7
• 238000011282 treatment Methods 0.000 claims description 7
• ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims description 6
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 6
• 150000001204 N-oxides Chemical class 0.000 claims description 6
• 230000001404 mediated effect Effects 0.000 claims description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
• 230000002018 overexpression Effects 0.000 claims description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• GJXUUDPBMCBINS-UHFFFAOYSA-N tert-butyl n-[5-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]pentyl]carbamate Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCCCNC(=O)OC(C)(C)C)N=CC=2)=N1 GJXUUDPBMCBINS-UHFFFAOYSA-N 0.000 claims description 6
• SRUUQKVZNDNFFD-UHFFFAOYSA-N 3,3-dimethyl-n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]butanamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(NC(=O)CC(C)(C)C)=NC3=N2)C=2N=C(N=CC=2)S(C)(=O)=O)=N1 SRUUQKVZNDNFFD-UHFFFAOYSA-N 0.000 claims description 5
• NQGDNOYOIMCELQ-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)-n-(2-oxo-2-pyridin-3-ylethyl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NCC(=O)C=2C=NC=CC=2)C=2N=C(N)N=CC=2)=N1 NQGDNOYOIMCELQ-UHFFFAOYSA-N 0.000 claims description 5
• ZSGAZWNRAGROEO-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)-n-(piperidin-3-ylmethyl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NCC2CNCCC2)C=2N=C(N)N=CC=2)=N1 ZSGAZWNRAGROEO-UHFFFAOYSA-N 0.000 claims description 5
• RIHSPLOZUDDXSE-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-methoxy-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NOC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 RIHSPLOZUDDXSE-UHFFFAOYSA-N 0.000 claims description 5
• RMHURWLBIXLSDK-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(1h-pyrazol-5-yl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NC=3NN=CC=3)N=CC=2)=N1 RMHURWLBIXLSDK-UHFFFAOYSA-N 0.000 claims description 5
• VHVLKQPXJUKJFV-SFHVURJKSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-[(1s)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1C(N1C=CC=CC1=N1)=C1C1=CC=CC(C)=N1 VHVLKQPXJUKJFV-SFHVURJKSA-N 0.000 claims description 5
• 206010019668 Hepatic fibrosis Diseases 0.000 claims description 5
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
• 238000009825 accumulation Methods 0.000 claims description 5
• 206010069351 acute lung injury Diseases 0.000 claims description 5
• ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 5
• 229940098779 methanesulfonic acid Drugs 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 5
• LHBQJBASKOAGGW-UHFFFAOYSA-N n,n-dimethyl-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CN(C)C1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 LHBQJBASKOAGGW-UHFFFAOYSA-N 0.000 claims description 5
• WWSCCUJUUTZBPL-UHFFFAOYSA-N n-(2-methoxyethyl)-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound COCCNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 WWSCCUJUUTZBPL-UHFFFAOYSA-N 0.000 claims description 5
• RQLBSRWECGGUKO-UHFFFAOYSA-N n-[(4-aminophenyl)methyl]-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCC=3C=CC(N)=CC=3)N=CC=2)=N1 RQLBSRWECGGUKO-UHFFFAOYSA-N 0.000 claims description 5
• OFYLYPTVTMOCTB-UHFFFAOYSA-N n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]propanamide Chemical compound N1=C2N=C(NC(=O)CC)C=CN2C(C=2N=C(SC)N=CC=2)=C1C1=CC=CC(C)=N1 OFYLYPTVTMOCTB-UHFFFAOYSA-N 0.000 claims description 5
• XNAAOIBANVQHDR-UHFFFAOYSA-N n-cyclopentyl-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NC3CCCC3)N=CC=2)=N1 XNAAOIBANVQHDR-UHFFFAOYSA-N 0.000 claims description 5
• BAFUGFTZYCDGRM-UHFFFAOYSA-N n-cyclopropyl-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NC3CC3)N=CC=2)=N1 BAFUGFTZYCDGRM-UHFFFAOYSA-N 0.000 claims description 5
• RRRGHOSHLCPQLU-UHFFFAOYSA-N n-methyl-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 RRRGHOSHLCPQLU-UHFFFAOYSA-N 0.000 claims description 5
• XPYZSOJKFJRHIS-UHFFFAOYSA-N tert-butyl n-[3-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]propyl]carbamate Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCNC(=O)OC(C)(C)C)N=CC=2)=N1 XPYZSOJKFJRHIS-UHFFFAOYSA-N 0.000 claims description 5
• FLMHPOCIZIPARJ-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CSC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 FLMHPOCIZIPARJ-UHFFFAOYSA-N 0.000 claims description 4
• TVCVBBJSTVIFLY-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-pyrimidin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC(N)=NC3=N2)C=2N=CN=CC=2)=N1 TVCVBBJSTVIFLY-UHFFFAOYSA-N 0.000 claims description 4
• XPQIPUZPSLAZDV-UHFFFAOYSA-N 2-pyridylethylamine Chemical compound NCCC1=CC=CC=N1 XPQIPUZPSLAZDV-UHFFFAOYSA-N 0.000 claims description 4
• QNKDCPDOULOXBJ-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-(2-hydroxyethyl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NCCO)C=2N=C(N)N=CC=2)=N1 QNKDCPDOULOXBJ-UHFFFAOYSA-N 0.000 claims description 4
• PTALXKKEJWSJGX-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-ethyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound N1=C2C=C(C(=O)NCC)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 PTALXKKEJWSJGX-UHFFFAOYSA-N 0.000 claims description 4
• AMODHECBNXJGPF-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-methoxy-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound N1=C2C=C(C(=O)NOC)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 AMODHECBNXJGPF-UHFFFAOYSA-N 0.000 claims description 4
• XRHDZRZVBYMLHG-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(2-pyridin-3-ylethyl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCC=3C=NC=CC=3)N=CC=2)=N1 XRHDZRZVBYMLHG-UHFFFAOYSA-N 0.000 claims description 4
• PGEFNWQUJQHPLE-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(2-pyridin-4-ylethyl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCC=3C=CN=CC=3)N=CC=2)=N1 PGEFNWQUJQHPLE-UHFFFAOYSA-N 0.000 claims description 4
• MYKNCPCNCPKGDH-UHFFFAOYSA-N 4-[2-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]ethyl]benzenesulfonamide Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCC=3C=CC(=CC=3)S(N)(=O)=O)N=CC=2)=N1 MYKNCPCNCPKGDH-UHFFFAOYSA-N 0.000 claims description 4
• 201000009030 Carcinoma Diseases 0.000 claims description 4
• 206010020772 Hypertension Diseases 0.000 claims description 4
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 4
• QEQJSRLUCZMVDY-UHFFFAOYSA-N [3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-6-yl]methanol Chemical compound CC1=CC=CC(C2=C(N3C=C(CO)C=CC3=N2)C=2N=C(N)N=CC=2)=N1 QEQJSRLUCZMVDY-UHFFFAOYSA-N 0.000 claims description 4
• ANTKYHGNIZRNTI-UHFFFAOYSA-N [3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-7-yl]methanol Chemical compound CC1=CC=CC(C2=C(N3C=CC(CO)=CC3=N2)C=2N=C(N)N=CC=2)=N1 ANTKYHGNIZRNTI-UHFFFAOYSA-N 0.000 claims description 4
• 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 4
• 208000017169 kidney disease Diseases 0.000 claims description 4
• 210000004185 liver Anatomy 0.000 claims description 4
• 210000004072 lung Anatomy 0.000 claims description 4
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 4
• YSFRQMGFXGXWMD-UHFFFAOYSA-N methyl 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxylate Chemical compound N12C=C(C(=O)OC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 YSFRQMGFXGXWMD-UHFFFAOYSA-N 0.000 claims description 4
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
• WEVPRMMAVXDFRH-UHFFFAOYSA-N n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]propanamide Chemical compound N1=C2N=C(NC(=O)CC)C=CN2C(C=2N=C(N=CC=2)S(C)(=O)=O)=C1C1=CC=CC(C)=N1 WEVPRMMAVXDFRH-UHFFFAOYSA-N 0.000 claims description 4
• YYAVSZGFEPUTHP-UHFFFAOYSA-N n-[3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyrimidin-7-yl]-2-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(CC(=O)NC2=NC3=NC(=C(N3C=C2)C=2N=C(N)N=CC=2)C=2N=C(C)C=CC=2)=C1 YYAVSZGFEPUTHP-UHFFFAOYSA-N 0.000 claims description 4
• QCWUMXGINRGKHD-UHFFFAOYSA-N n-[3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyrimidin-7-yl]-3,3-dimethylbutanamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(NC(=O)CC(C)(C)C)=NC3=N2)C=2N=C(N)N=CC=2)=N1 QCWUMXGINRGKHD-UHFFFAOYSA-N 0.000 claims description 4
• RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 claims description 4
• 238000001959 radiotherapy Methods 0.000 claims description 4
• 210000004881 tumor cell Anatomy 0.000 claims description 4
• QBVDQHQMPZYGCP-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-piperidin-1-ylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)N2CCCCC2)=N1 QBVDQHQMPZYGCP-UHFFFAOYSA-N 0.000 claims description 3
• ZXZQBJLOMCZQHF-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-pyrrolidin-1-ylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)N2CCCC2)=N1 ZXZQBJLOMCZQHF-UHFFFAOYSA-N 0.000 claims description 3
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 3
• NAHHNSMHYCLMON-UHFFFAOYSA-N 2-pyridin-3-ylethanamine Chemical compound NCCC1=CC=CN=C1 NAHHNSMHYCLMON-UHFFFAOYSA-N 0.000 claims description 3
• IDLHTECVNDEOIY-UHFFFAOYSA-N 2-pyridin-4-ylethanamine Chemical compound NCCC1=CC=NC=C1 IDLHTECVNDEOIY-UHFFFAOYSA-N 0.000 claims description 3
• IDWPHPUVJLLXHG-UHFFFAOYSA-N 3,3-dimethyl-n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]butanamide Chemical compound CSC1=NC=CC(C=2N3C=CC(NC(=O)CC(C)(C)C)=NC3=NC=2C=2N=C(C)C=CC=2)=N1 IDWPHPUVJLLXHG-UHFFFAOYSA-N 0.000 claims description 3
• VDVOBHGYLRGHPS-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)-n-(2-thiophen-2-ylethyl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C(=O)NCCC=2SC=CC=2)C=2N=C(N)N=CC=2)=N1 VDVOBHGYLRGHPS-UHFFFAOYSA-N 0.000 claims description 3
• WBSWEUKONANKOY-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(N)=O)C=2N=C(N)N=CC=2)=N1 WBSWEUKONANKOY-UHFFFAOYSA-N 0.000 claims description 3
• GNCJJLAGVLNJOB-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-6-methyl-2-(6-methylpyridin-2-yl)-n-(2-pyridin-2-ylethyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C12=NC(C=3N=C(C)C=CC=3)=C(C=3N=C(N)N=CC=3)N2C=C(C)C=C1NCCC1=CC=CC=N1 GNCJJLAGVLNJOB-UHFFFAOYSA-N 0.000 claims description 3
• HMBBFJLPVIOKEQ-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-6-methyl-2-(6-methylpyridin-2-yl)-n-(3-morpholin-4-ylpropyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C12=NC(C=3N=C(C)C=CC=3)=C(C=3N=C(N)N=CC=3)N2C=C(C)C=C1NCCCN1CCOCC1 HMBBFJLPVIOKEQ-UHFFFAOYSA-N 0.000 claims description 3
• DZASFVSKVJGYPH-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-N-hydroxy-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NO)C=2N=C(N)N=CC=2)=N1 DZASFVSKVJGYPH-UHFFFAOYSA-N 0.000 claims description 3
• VKODDBPPNQPIEV-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n',n'-dimethyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carbohydrazide Chemical compound N1=C2C=C(C(=O)NN(C)C)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 VKODDBPPNQPIEV-UHFFFAOYSA-N 0.000 claims description 3
• WMBVVXOGMONONM-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-[2-(dimethylamino)ethyl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NCCN(C)C)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 WMBVVXOGMONONM-UHFFFAOYSA-N 0.000 claims description 3
• ZFGJPLYSVPCNAA-UHFFFAOYSA-N 3-(2-methylsulfanylpyrimidin-4-yl)-2-pyridin-2-ylimidazo[1,2-a]pyridine Chemical compound CSC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=CC=CC=2)=N1 ZFGJPLYSVPCNAA-UHFFFAOYSA-N 0.000 claims description 3
• CRXCBJUEAVHWOS-UHFFFAOYSA-N 3-[2-(2-methylaziridin-1-yl)pyrimidin-4-yl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine Chemical compound CC1CN1C1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 CRXCBJUEAVHWOS-UHFFFAOYSA-N 0.000 claims description 3
• NKZVQBJACLKGJT-UHFFFAOYSA-N 3-[2-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine Chemical compound C1CN(C)CCN1C1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 NKZVQBJACLKGJT-UHFFFAOYSA-N 0.000 claims description 3
• XAZXLZNLGFUKFB-UHFFFAOYSA-N 3-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]phenol Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NC=3C=C(O)C=CC=3)N=CC=2)=N1 XAZXLZNLGFUKFB-UHFFFAOYSA-N 0.000 claims description 3
• YBHWFXBSFOTTDF-UHFFFAOYSA-N 4-[2-(6-chloropyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(Cl)C=CC=2)=N1 YBHWFXBSFOTTDF-UHFFFAOYSA-N 0.000 claims description 3
• ZIKNHXBNMFKMFV-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(2-morpholin-4-ylethyl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCN3CCOCC3)N=CC=2)=N1 ZIKNHXBNMFKMFV-UHFFFAOYSA-N 0.000 claims description 3
• UMUBGGWVFYWKPC-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(2-pyridin-2-ylethyl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCC=3N=CC=CC=3)N=CC=2)=N1 UMUBGGWVFYWKPC-UHFFFAOYSA-N 0.000 claims description 3
• OXNVLQQCADIKLE-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(3-morpholin-4-ylpropyl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCN3CCOCC3)N=CC=2)=N1 OXNVLQQCADIKLE-UHFFFAOYSA-N 0.000 claims description 3
• AMZCVYMZEGXAJP-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidine-2-carbonitrile Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)C#N)=N1 AMZCVYMZEGXAJP-UHFFFAOYSA-N 0.000 claims description 3
• XBQDWPKMVWEZHR-UHFFFAOYSA-N 4-[6-chloro-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=C(Cl)C=CC3=N2)C=2N=C(N)N=CC=2)=N1 XBQDWPKMVWEZHR-UHFFFAOYSA-N 0.000 claims description 3
• JNYLMODTPLSLIF-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine-3-carboxylic acid Chemical group OC(=O)C1=CC=C(C(F)(F)F)N=C1 JNYLMODTPLSLIF-UHFFFAOYSA-N 0.000 claims description 3
• ZTXZDMPLXAIHOB-UHFFFAOYSA-N 6-fluoro-2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CSC1=NC=CC(C=2N3C=C(F)C=CC3=NC=2C=2N=C(C)C=CC=2)=N1 ZTXZDMPLXAIHOB-UHFFFAOYSA-N 0.000 claims description 3
• 239000005711 Benzoic acid Substances 0.000 claims description 3
• 206010004664 Biliary fibrosis Diseases 0.000 claims description 3
• 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 3
• 208000007659 Fibroadenoma Diseases 0.000 claims description 3
• 201000008808 Fibrosarcoma Diseases 0.000 claims description 3
• 208000032612 Glial tumor Diseases 0.000 claims description 3
• 206010018338 Glioma Diseases 0.000 claims description 3
• 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 3
• 208000005777 Lupus Nephritis Diseases 0.000 claims description 3
• 206010027476 Metastases Diseases 0.000 claims description 3
• 208000034578 Multiple myelomas Diseases 0.000 claims description 3
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
• 206010039710 Scleroderma Diseases 0.000 claims description 3
• 206010046798 Uterine leiomyoma Diseases 0.000 claims description 3
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 3
• 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 3
• 125000005015 aryl alkynyl group Chemical group 0.000 claims description 3
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 3
• 210000003445 biliary tract Anatomy 0.000 claims description 3
• 210000000481 breast Anatomy 0.000 claims description 3
• 230000009787 cardiac fibrosis Effects 0.000 claims description 3
• 210000003169 central nervous system Anatomy 0.000 claims description 3
• 210000003679 cervix uteri Anatomy 0.000 claims description 3
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 3
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 3
• 208000033679 diabetic kidney disease Diseases 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• IGVJTFHMBDHFBX-UHFFFAOYSA-N ethyl 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxylate Chemical compound N1=C2C=C(C(=O)OCC)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 IGVJTFHMBDHFBX-UHFFFAOYSA-N 0.000 claims description 3
• 206010016629 fibroma Diseases 0.000 claims description 3
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
• 208000005017 glioblastoma Diseases 0.000 claims description 3
• 210000003128 head Anatomy 0.000 claims description 3
• 230000002440 hepatic effect Effects 0.000 claims description 3
• 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims description 3
• 201000010260 leiomyoma Diseases 0.000 claims description 3
• 201000001441 melanoma Diseases 0.000 claims description 3
• 230000009401 metastasis Effects 0.000 claims description 3
• WSIRNNCRNKOMOB-UHFFFAOYSA-N methyl 3-[[3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carbonyl]amino]propanoate Chemical compound N1=C2C=C(C(=O)NCCC(=O)OC)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 WSIRNNCRNKOMOB-UHFFFAOYSA-N 0.000 claims description 3
• IMZHFBNWTRKGPJ-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCN3C=NC=C3)N=CC=2)=N1 IMZHFBNWTRKGPJ-UHFFFAOYSA-N 0.000 claims description 3
• IHMOMVMNTVXNDN-UHFFFAOYSA-N n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]-3-pyridin-3-ylpropanamide Chemical compound CSC1=NC=CC(C=2N3C=CC(NC(=O)CCC=4C=NC=CC=4)=NC3=NC=2C=2N=C(C)C=CC=2)=N1 IHMOMVMNTVXNDN-UHFFFAOYSA-N 0.000 claims description 3
• AXAGAGTVHZOYQD-UHFFFAOYSA-N n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]-3-pyridin-3-ylpropanamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(NC(=O)CCC=4C=NC=CC=4)=NC3=N2)C=2N=C(N=CC=2)S(C)(=O)=O)=N1 AXAGAGTVHZOYQD-UHFFFAOYSA-N 0.000 claims description 3
• LNJWCRITIZFPCK-UHFFFAOYSA-N n-[2-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]ethyl]acetamide Chemical compound CC(=O)NCCNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 LNJWCRITIZFPCK-UHFFFAOYSA-N 0.000 claims description 3
• XCFCMXMGTBEOGF-UHFFFAOYSA-N n-[3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyrimidin-7-yl]pyridine-3-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(NC(=O)C=4C=NC=CC=4)=NC3=N2)C=2N=C(N)N=CC=2)=N1 XCFCMXMGTBEOGF-UHFFFAOYSA-N 0.000 claims description 3
• MCXIJRXEPGHSNX-UHFFFAOYSA-N n-[3-(4-methylpiperazin-1-yl)propyl]-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1CCCNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 MCXIJRXEPGHSNX-UHFFFAOYSA-N 0.000 claims description 3
• OOBORGGKBQGOQB-UHFFFAOYSA-N n-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]acetamide Chemical compound CC(=O)NC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 OOBORGGKBQGOQB-UHFFFAOYSA-N 0.000 claims description 3
• 210000003739 neck Anatomy 0.000 claims description 3
• 210000000496 pancreas Anatomy 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 210000002307 prostate Anatomy 0.000 claims description 3
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 3
• KSGUWWVYVKIXKD-UHFFFAOYSA-N tert-butyl n-[4-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]butyl]carbamate Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCCNC(=O)OC(C)(C)C)N=CC=2)=N1 KSGUWWVYVKIXKD-UHFFFAOYSA-N 0.000 claims description 3
• QOFZZTBWWJNFCA-UHFFFAOYSA-N texas red-X Chemical compound [O-]S(=O)(=O)C1=CC(S(=O)(=O)NCCCCCC(=O)O)=CC=C1C(C1=CC=2CCCN3CCCC(C=23)=C1O1)=C2C1=C(CCC1)C3=[N+]1CCCC3=C2 QOFZZTBWWJNFCA-UHFFFAOYSA-N 0.000 claims description 3
• 229920002554 vinyl polymer Polymers 0.000 claims description 3
• 230000029663 wound healing Effects 0.000 claims description 3
• GIJBVTBOMJGKKK-UHFFFAOYSA-N 2-(3-amino-6-iminoxanthen-9-yl)-4-[4-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]butylcarbamoyl]benzoic acid Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCCNC(=O)C=3C=C(C(C(O)=O)=CC=3)C3=C4C=CC(=N)C=C4OC4=CC(N)=CC=C43)N=CC=2)=N1 GIJBVTBOMJGKKK-UHFFFAOYSA-N 0.000 claims description 2
• WVAVXRCQIICYRN-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-pyrimidin-4-ylimidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=CN=CC=2)=N1 WVAVXRCQIICYRN-UHFFFAOYSA-N 0.000 claims description 2
• DZYLDAACLSDXJN-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-6-methyl-2-(6-methylpyridin-2-yl)-n-(2-pyridin-4-ylethyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C12=NC(C=3N=C(C)C=CC=3)=C(C=3N=C(N)N=CC=3)N2C=C(C)C=C1NCCC1=CC=NC=C1 DZYLDAACLSDXJN-UHFFFAOYSA-N 0.000 claims description 2
• WOBVNDLMPGASJH-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-(2-methoxyethyl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NCCOC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 WOBVNDLMPGASJH-UHFFFAOYSA-N 0.000 claims description 2
• DSZXRZARDVKLEJ-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-[2-(dimethylamino)ethyl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound N1=C2C=C(C(=O)NCCN(C)C)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 DSZXRZARDVKLEJ-UHFFFAOYSA-N 0.000 claims description 2
• HWDOSLVNGNQUSJ-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-cyclopropyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C(=O)NC2CC2)C=2N=C(N)N=CC=2)=N1 HWDOSLVNGNQUSJ-UHFFFAOYSA-N 0.000 claims description 2
• IUXZYJGBRTUWHZ-UHFFFAOYSA-N 4-(2-pyridin-2-ylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=CC=CC=2)=N1 IUXZYJGBRTUWHZ-UHFFFAOYSA-N 0.000 claims description 2
• VHVLKQPXJUKJFV-GOSISDBHSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-[(1r)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1C(N1C=CC=CC1=N1)=C1C1=CC=CC(C)=N1 VHVLKQPXJUKJFV-GOSISDBHSA-N 0.000 claims description 2
• PUMALOKTAVGLKL-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidine-2-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)C(N)=O)=N1 PUMALOKTAVGLKL-UHFFFAOYSA-N 0.000 claims description 2
• JMHSCWJIDIKGNZ-UHFFFAOYSA-N 4-carbamoylbenzoic acid Chemical compound NC(=O)C1=CC=C(C(O)=O)C=C1 JMHSCWJIDIKGNZ-UHFFFAOYSA-N 0.000 claims description 2
• BBEQQKBWUHCIOU-UHFFFAOYSA-N 5-(dimethylamino)-1-naphthalenesulfonic acid(dansyl acid) Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(O)(=O)=O BBEQQKBWUHCIOU-UHFFFAOYSA-N 0.000 claims description 2
• SWIZVVDXYOFXQN-UHFFFAOYSA-N 6-bromo-2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CSC1=NC=CC(C=2N3C=C(Br)C=CC3=NC=2C=2N=C(C)C=CC=2)=N1 SWIZVVDXYOFXQN-UHFFFAOYSA-N 0.000 claims description 2
• BJQWTQKNTPVPHU-UHFFFAOYSA-N 7-amino-4-methyl-3-[2-[4-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]butylamino]-2-oxoethyl]-2-oxochromene-6-sulfonic acid Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCCNC(=O)CC=3C(OC4=CC(N)=C(C=C4C=3C)S(O)(=O)=O)=O)N=CC=2)=N1 BJQWTQKNTPVPHU-UHFFFAOYSA-N 0.000 claims description 2
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 2
• 208000024827 Alzheimer disease Diseases 0.000 claims description 2
• 206010059245 Angiopathy Diseases 0.000 claims description 2
• 200000000007 Arterial disease Diseases 0.000 claims description 2
• 206010008609 Cholangitis sclerosing Diseases 0.000 claims description 2
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
• 208000016192 Demyelinating disease Diseases 0.000 claims description 2
• 206010012305 Demyelination Diseases 0.000 claims description 2
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
• 208000002260 Keloid Diseases 0.000 claims description 2
• 206010023330 Keloid scar Diseases 0.000 claims description 2
• 208000004852 Lung Injury Diseases 0.000 claims description 2
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 2
• 206010069363 Traumatic lung injury Diseases 0.000 claims description 2
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 2
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 2
• 230000002490 cerebral effect Effects 0.000 claims description 2
• 238000002512 chemotherapy Methods 0.000 claims description 2
• 208000018631 connective tissue disease Diseases 0.000 claims description 2
• 229940079593 drug Drugs 0.000 claims description 2
• MLLZUQFQTCAQEX-UHFFFAOYSA-N ethyl 2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridine-7-carboxylate Chemical compound N1=C2C=C(C(=O)OCC)C=CN2C(C=2N=C(N=CC=2)S(C)(=O)=O)=C1C1=CC=CC(C)=N1 MLLZUQFQTCAQEX-UHFFFAOYSA-N 0.000 claims description 2
• 125000004494 ethyl ester group Chemical group 0.000 claims description 2
• 208000010706 fatty liver disease Diseases 0.000 claims description 2
• 210000001117 keloid Anatomy 0.000 claims description 2
• 208000032839 leukemia Diseases 0.000 claims description 2
• 231100000515 lung injury Toxicity 0.000 claims description 2
• PGCUQJWVGDBCCN-UHFFFAOYSA-N methyl 2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridine-6-carboxylate Chemical compound N12C=C(C(=O)OC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(S(C)(=O)=O)=N1 PGCUQJWVGDBCCN-UHFFFAOYSA-N 0.000 claims description 2
• 201000006417 multiple sclerosis Diseases 0.000 claims description 2
• SKUDIQGDJCJNBP-UHFFFAOYSA-N n',n'-dimethyl-n-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]ethane-1,2-diamine Chemical compound CN(C)CCNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 SKUDIQGDJCJNBP-UHFFFAOYSA-N 0.000 claims description 2
• VKJINYHQKFWPDV-UHFFFAOYSA-N n-(2-aminoethyl)-3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NCCN)C=2N=C(N)N=CC=2)=N1 VKJINYHQKFWPDV-UHFFFAOYSA-N 0.000 claims description 2
• VXYQMZJVBIOSHZ-UHFFFAOYSA-N n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]pyridine-3-carboxamide Chemical compound CSC1=NC=CC(C=2N3C=CC(NC(=O)C=4C=NC=CC=4)=NC3=NC=2C=2N=C(C)C=CC=2)=N1 VXYQMZJVBIOSHZ-UHFFFAOYSA-N 0.000 claims description 2
• RYFGJBIOMCAFFZ-UHFFFAOYSA-N n-[3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyrimidin-7-yl]propanamide Chemical compound N1=C2N=C(NC(=O)CC)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 RYFGJBIOMCAFFZ-UHFFFAOYSA-N 0.000 claims description 2
• BCXKGIAQNYLJGM-UHFFFAOYSA-N n-[4-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]butyl]acetamide Chemical compound CC(=O)NCCCCNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 BCXKGIAQNYLJGM-UHFFFAOYSA-N 0.000 claims description 2
• 210000002569 neuron Anatomy 0.000 claims description 2
• 210000001672 ovary Anatomy 0.000 claims description 2
• 201000000742 primary sclerosing cholangitis Diseases 0.000 claims description 2
• VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 2
• 208000037803 restenosis Diseases 0.000 claims description 2
• 208000010157 sclerosing cholangitis Diseases 0.000 claims description 2
• 208000020431 spinal cord injury Diseases 0.000 claims description 2
• 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
• VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 claims 3
• GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims 3
• UYQAOMNHPUTELT-UHFFFAOYSA-N n-[3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyrimidin-7-yl]-3-pyridin-3-ylpropanamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(NC(=O)CCC=4C=NC=CC=4)=NC3=N2)C=2N=C(N)N=CC=2)=N1 UYQAOMNHPUTELT-UHFFFAOYSA-N 0.000 claims 3
• UDWZGKJGQUDLSG-UHFFFAOYSA-N 4-(2-pyridin-2-ylimidazo[1,2-a]pyridin-3-yl)-n-(pyridin-3-ylmethyl)pyrimidin-2-amine Chemical compound C=1C=CN=CC=1CNC(N=1)=NC=CC=1C(N1C=CC=CC1=N1)=C1C1=CC=CC=N1 UDWZGKJGQUDLSG-UHFFFAOYSA-N 0.000 claims 2
• GLWTXYIDCICEOP-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-propan-2-ylpyrimidin-2-amine Chemical compound CC(C)NC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 GLWTXYIDCICEOP-UHFFFAOYSA-N 0.000 claims 2
• QVXCQUWCCGYXPM-UHFFFAOYSA-N 4-[7-(aminomethyl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC(CN)=CC3=N2)C=2N=C(N)N=CC=2)=N1 QVXCQUWCCGYXPM-UHFFFAOYSA-N 0.000 claims 2
• BVOUXZMZTDMVGT-UHFFFAOYSA-N 4-[7-methyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound N1=C2C=C(C)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 BVOUXZMZTDMVGT-UHFFFAOYSA-N 0.000 claims 2
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 2
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
• 150000004985 diamines Chemical class 0.000 claims 2
• JYJCLZJDOYHSJZ-UHFFFAOYSA-N n-[3-(4-methylpiperidin-1-yl)propyl]-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1CC(C)CCN1CCCNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 JYJCLZJDOYHSJZ-UHFFFAOYSA-N 0.000 claims 2
• GAXOXEQTVABLDL-UHFFFAOYSA-N n-cyclobutyl-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NC3CCC3)N=CC=2)=N1 GAXOXEQTVABLDL-UHFFFAOYSA-N 0.000 claims 2
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 2
• QFVDOHIBLYRLPY-UHFFFAOYSA-N 2-(2,7-difluoro-3-hydroxy-6-oxoxanthen-9-yl)-5-[4-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]butylcarbamoyl]benzoic acid Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCCNC(=O)C=3C=C(C(=CC=3)C3=C4C=C(F)C(=O)C=C4OC4=CC(O)=C(F)C=C43)C(O)=O)N=CC=2)=N1 QFVDOHIBLYRLPY-UHFFFAOYSA-N 0.000 claims 1
• PMPGOGWILLVGCS-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-8-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=C(N)C3=N2)C=2N=C(N)N=CC=2)=N1 PMPGOGWILLVGCS-UHFFFAOYSA-N 0.000 claims 1
• BAUQEWQBBHXUMG-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C#N)C=2N=C(N)N=CC=2)=N1 BAUQEWQBBHXUMG-UHFFFAOYSA-N 0.000 claims 1
• JJRWXPAUYRHWSS-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC(N)=NC3=N2)C=2N=C(N)N=CC=2)=N1 JJRWXPAUYRHWSS-UHFFFAOYSA-N 0.000 claims 1
• GRZYOCPOBQZHDY-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-6-methyl-2-(6-methylpyridin-2-yl)-n-(2-morpholin-4-ylethyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C12=NC(C=3N=C(C)C=CC=3)=C(C=3N=C(N)N=CC=3)N2C=C(C)C=C1NCCN1CCOCC1 GRZYOCPOBQZHDY-UHFFFAOYSA-N 0.000 claims 1
• MPPCLPUSEFDPGS-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-(1,4-dioxan-2-ylmethyl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NCC2OCCOC2)C=2N=C(N)N=CC=2)=N1 MPPCLPUSEFDPGS-UHFFFAOYSA-N 0.000 claims 1
• UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 claims 1
• DKWLODKAWHEALD-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(3-piperidin-1-ylpropyl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCN3CCCCC3)N=CC=2)=N1 DKWLODKAWHEALD-UHFFFAOYSA-N 0.000 claims 1
• BBOXUBICUADAOW-UHFFFAOYSA-N 4-[6-bromo-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=C(Br)C=CC3=N2)C=2N=C(N)N=CC=2)=N1 BBOXUBICUADAOW-UHFFFAOYSA-N 0.000 claims 1
• OARUIIZSOREFDH-UHFFFAOYSA-N 4-[6-fluoro-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=C(F)C=CC3=N2)C=2N=C(N)N=CC=2)=N1 OARUIIZSOREFDH-UHFFFAOYSA-N 0.000 claims 1
• SIRPCTMBJICDAX-UHFFFAOYSA-N 4-[6-methyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound N12C=C(C)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 SIRPCTMBJICDAX-UHFFFAOYSA-N 0.000 claims 1
• BPNIKRRCKQDOMY-UHFFFAOYSA-N 4-[8-methyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=C(C)C3=N2)C=2N=C(N)N=CC=2)=N1 BPNIKRRCKQDOMY-UHFFFAOYSA-N 0.000 claims 1
• WQKHERPPDYPMNX-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(Cl)=CC=C21 WQKHERPPDYPMNX-UHFFFAOYSA-N 0.000 claims 1
• 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 1
• 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 1
• 208000012654 Primary biliary cholangitis Diseases 0.000 claims 1
• JTTAWSWSUAVCDG-UHFFFAOYSA-N [2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridin-6-yl]methanol Chemical compound CC1=CC=CC(C2=C(N3C=C(CO)C=CC3=N2)C=2N=C(N=CC=2)S(C)(=O)=O)=N1 JTTAWSWSUAVCDG-UHFFFAOYSA-N 0.000 claims 1
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
• 125000001475 halogen functional group Chemical group 0.000 claims 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
• HUFJMAZLBLCKBL-UHFFFAOYSA-N methyl 2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyridine-6-carboxylate Chemical compound N12C=C(C(=O)OC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(SC)=N1 HUFJMAZLBLCKBL-UHFFFAOYSA-N 0.000 claims 1
• VXTGVZRNWICVJF-UHFFFAOYSA-N n-[3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyrimidin-7-yl]acetamide Chemical compound N1=C2N=C(NC(=O)C)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 VXTGVZRNWICVJF-UHFFFAOYSA-N 0.000 claims 1
• 235000005152 nicotinamide Nutrition 0.000 claims 1
• 201000002793 renal fibrosis Diseases 0.000 claims 1
• LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 description 165
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 133
• 238000002360 preparation method Methods 0.000 description 103
• 239000007787 solid Substances 0.000 description 100
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 86
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 73
• 239000000243 solution Substances 0.000 description 65
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 59
• 238000005481 NMR spectroscopy Methods 0.000 description 58
• 239000002002 slurry Substances 0.000 description 58
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 54
• 239000000203 mixture Substances 0.000 description 54
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 47
• 238000004128 high performance liquid chromatography Methods 0.000 description 45
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
• 238000005160 1H NMR spectroscopy Methods 0.000 description 33
• 239000002244 precipitate Substances 0.000 description 33
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 32
• 108020003175 receptors Proteins 0.000 description 32
• 102000005962 receptors Human genes 0.000 description 32
• 108010059616 Activins Proteins 0.000 description 31
• 102000005606 Activins Human genes 0.000 description 31
• 239000000488 activin Substances 0.000 description 31
• 238000010992 reflux Methods 0.000 description 31
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• 239000007821 HATU Substances 0.000 description 25
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 25
• 238000004007 reversed phase HPLC Methods 0.000 description 25
• 238000003756 stirring Methods 0.000 description 25
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 24
• 229960000583 acetic acid Drugs 0.000 description 22
• 239000000463 material Substances 0.000 description 22
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
• 230000003197 catalytic effect Effects 0.000 description 20
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 17
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 16
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• 239000011734 sodium Substances 0.000 description 15
• 230000000694 effects Effects 0.000 description 13
• QWMFKVNJIYNWII-UHFFFAOYSA-N 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(Br)C=N1 QWMFKVNJIYNWII-UHFFFAOYSA-N 0.000 description 12
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 12
• ZEMZPXWZVTUONV-UHFFFAOYSA-N 2-(2-dicyclohexylphosphanylphenyl)-n,n-dimethylaniline Chemical group CN(C)C1=CC=CC=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 ZEMZPXWZVTUONV-UHFFFAOYSA-N 0.000 description 11
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
• 239000012267 brine Substances 0.000 description 11
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
• 230000015572 biosynthetic process Effects 0.000 description 10
• 229910052794 bromium Inorganic materials 0.000 description 10
• 239000000872 buffer Substances 0.000 description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
• 238000002953 preparative HPLC Methods 0.000 description 10
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
• 235000019439 ethyl acetate Nutrition 0.000 description 9
• 239000012074 organic phase Substances 0.000 description 9
• 125000001424 substituent group Chemical group 0.000 description 9
• LHLYSNGWIOFMRY-UHFFFAOYSA-N 1-(6-methylpyridin-2-yl)-2-(2-methylsulfanylpyrimidin-4-yl)ethanone Chemical compound CSC1=NC=CC(CC(=O)C=2N=C(C)C=CC=2)=N1 LHLYSNGWIOFMRY-UHFFFAOYSA-N 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• 239000012362 glacial acetic acid Substances 0.000 description 8
• 229910000042 hydrogen bromide Inorganic materials 0.000 description 8
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 8
• 238000012360 testing method Methods 0.000 description 8
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 7
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
• 239000000908 ammonium hydroxide Substances 0.000 description 7
• 239000005557 antagonist Substances 0.000 description 7
• 238000003556 assay Methods 0.000 description 7
• 230000027455 binding Effects 0.000 description 7
• 239000000460 chlorine Substances 0.000 description 7
• 125000002883 imidazolyl group Chemical group 0.000 description 7
• 230000005764 inhibitory process Effects 0.000 description 7
• 229910052757 nitrogen Inorganic materials 0.000 description 7
• NWGPLYYBECWONP-UHFFFAOYSA-N (carbamoylamino) hydrogen sulfate Chemical compound NC(=O)NOS(O)(=O)=O NWGPLYYBECWONP-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 125000004043 oxo group Chemical group O=* 0.000 description 6
• 230000001225 therapeutic effect Effects 0.000 description 6
• 125000004432 carbon atom Chemical group C* 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 239000005090 green fluorescent protein Substances 0.000 description 5
• PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
• 230000000750 progressive effect Effects 0.000 description 5
• 108090000623 proteins and genes Proteins 0.000 description 5
• JDUXZIDJZQSKOX-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyridine-7-carboxylic acid Chemical compound CC1=NC(=CC=C1)C2=C(N3C=CC(=CC3=N2)C(=O)O)C4=NC(=NC=C4)SC JDUXZIDJZQSKOX-UHFFFAOYSA-N 0.000 description 4
• UDJDYAIQOCLNCR-UHFFFAOYSA-N 4-[8-bromo-6-methyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound N12C=C(C)C=C(Br)C2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 UDJDYAIQOCLNCR-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• 102000008186 Collagen Human genes 0.000 description 4
• 108010035532 Collagen Proteins 0.000 description 4
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
• 239000005089 Luciferase Substances 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• 229910004298 SiO 2 Inorganic materials 0.000 description 4
• XECULGSXZDNXJQ-UHFFFAOYSA-N [2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyridin-6-yl]methanol Chemical compound CSC1=NC=CC(C=2N3C=C(CO)C=CC3=NC=2C=2N=C(C)C=CC=2)=N1 XECULGSXZDNXJQ-UHFFFAOYSA-N 0.000 description 4
• 239000008346 aqueous phase Substances 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 229920001436 collagen Polymers 0.000 description 4
• 125000000392 cycloalkenyl group Chemical group 0.000 description 4
• 239000006274 endogenous ligand Substances 0.000 description 4
• 230000014509 gene expression Effects 0.000 description 4
• 238000004519 manufacturing process Methods 0.000 description 4
• 239000012299 nitrogen atmosphere Substances 0.000 description 4
• 239000000546 pharmaceutical excipient Substances 0.000 description 4
• 125000003226 pyrazolyl group Chemical group 0.000 description 4
• 125000004076 pyridyl group Chemical group 0.000 description 4
• 125000006413 ring segment Chemical group 0.000 description 4
• DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 4
• 238000003786 synthesis reaction Methods 0.000 description 4
• 125000003831 tetrazolyl group Chemical group 0.000 description 4
• UBWXUGDQUBIEIZ-UHFFFAOYSA-N (13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl) 3-phenylpropanoate Chemical compound CC12CCC(C3CCC(=O)C=C3CC3)C3C1CCC2OC(=O)CCC1=CC=CC=C1 UBWXUGDQUBIEIZ-UHFFFAOYSA-N 0.000 description 3
• QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 description 3
• UCERVHYBSTYCQS-UHFFFAOYSA-N 4-methyl-2-methylsulfanylpyrimidine Chemical compound CSC1=NC=CC(C)=N1 UCERVHYBSTYCQS-UHFFFAOYSA-N 0.000 description 3
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 3
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 3
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
• 108010043121 Green Fluorescent Proteins Proteins 0.000 description 3
• 102000004144 Green Fluorescent Proteins Human genes 0.000 description 3
• 102400000401 Latency-associated peptide Human genes 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• 241000124008 Mammalia Species 0.000 description 3
• 102100025751 Mothers against decapentaplegic homolog 2 Human genes 0.000 description 3
• 101710143123 Mothers against decapentaplegic homolog 2 Proteins 0.000 description 3
• 102100025748 Mothers against decapentaplegic homolog 3 Human genes 0.000 description 3
• 101710143111 Mothers against decapentaplegic homolog 3 Proteins 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• 108010029485 Protein Isoforms Proteins 0.000 description 3
• 102000001708 Protein Isoforms Human genes 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
• 102000009618 Transforming Growth Factors Human genes 0.000 description 3
• 108010009583 Transforming Growth Factors Proteins 0.000 description 3
• 125000001931 aliphatic group Chemical group 0.000 description 3
• 230000035578 autophosphorylation Effects 0.000 description 3
• 230000008901 benefit Effects 0.000 description 3
• 201000011510 cancer Diseases 0.000 description 3
• 230000001413 cellular effect Effects 0.000 description 3
• 239000003102 growth factor Substances 0.000 description 3
• 125000005842 heteroatom Chemical group 0.000 description 3
• 125000004366 heterocycloalkenyl group Chemical group 0.000 description 3
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 3
• 239000003446 ligand Substances 0.000 description 3
• 230000004048 modification Effects 0.000 description 3
• 238000012986 modification Methods 0.000 description 3
• 230000001575 pathological effect Effects 0.000 description 3
• 208000005069 pulmonary fibrosis Diseases 0.000 description 3
• 230000004044 response Effects 0.000 description 3
• 210000002966 serum Anatomy 0.000 description 3
• 230000011664 signaling Effects 0.000 description 3
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
• 235000017557 sodium bicarbonate Nutrition 0.000 description 3
• WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 3
• 239000002904 solvent Substances 0.000 description 3
• 239000000758 substrate Substances 0.000 description 3
• 210000001519 tissue Anatomy 0.000 description 3
• YUXKOWPNKJSTPQ-AXWWPMSFSA-N (2s,3r)-2-amino-3-hydroxybutanoic acid;(2s)-2-amino-3-hydroxypropanoic acid Chemical compound OC[C@H](N)C(O)=O.C[C@@H](O)[C@H](N)C(O)=O YUXKOWPNKJSTPQ-AXWWPMSFSA-N 0.000 description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
• IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 2
• MCMKSMNPHIBOLT-UHFFFAOYSA-N 2-(3-methoxyphenyl)-n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]acetamide Chemical compound COC1=CC=CC(CC(=O)NC2=NC3=NC(=C(N3C=C2)C=2N=C(N=CC=2)S(C)(=O)=O)C=2N=C(C)C=CC=2)=C1 MCMKSMNPHIBOLT-UHFFFAOYSA-N 0.000 description 2
• IYTJQGUUWQZKMH-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-[2-(2h-tetrazol-5-yl)pyrimidin-4-yl]imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)C=2NN=NN=2)=N1 IYTJQGUUWQZKMH-UHFFFAOYSA-N 0.000 description 2
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
• YWJXDLAGSVQNRE-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-6-methyl-2-(6-methylpyridin-2-yl)-n-(2-pyridin-3-ylethyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C12=NC(C=3N=C(C)C=CC=3)=C(C=3N=C(N)N=CC=3)N2C=C(C)C=C1NCCC1=CC=CN=C1 YWJXDLAGSVQNRE-UHFFFAOYSA-N 0.000 description 2
• SVVCBKPGSAZAIZ-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-(1,4-dioxan-2-ylmethyl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C(=O)NCC2OCCOC2)C=2N=C(N)N=CC=2)=N1 SVVCBKPGSAZAIZ-UHFFFAOYSA-N 0.000 description 2
• ITDLSWQHTALTPU-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)pyrimidin-4-yl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)N2CCC2)=N1 ITDLSWQHTALTPU-UHFFFAOYSA-N 0.000 description 2
• UDPIROHVSULNKG-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N)N=CC=2)=N1 UDPIROHVSULNKG-UHFFFAOYSA-N 0.000 description 2
• TYUINBRGEGXQGY-UHFFFAOYSA-N 6-[6-methyl-2-(6-methylpyridin-2-yl)-8-(2-pyridin-4-ylethylamino)imidazo[1,2-a]pyridin-3-yl]-1h-pyrimidin-2-one Chemical compound C12=NC(C=3N=C(C)C=CC=3)=C(C=3N=C(O)N=CC=3)N2C=C(C)C=C1NCCC1=CC=NC=C1 TYUINBRGEGXQGY-UHFFFAOYSA-N 0.000 description 2
• VIRLLLRMQBHWCT-UHFFFAOYSA-N 6-chloro-2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=C(Cl)C=CC3=N2)C=2N=C(N=CC=2)S(C)(=O)=O)=N1 VIRLLLRMQBHWCT-UHFFFAOYSA-N 0.000 description 2
• PJCQKRMVXDOQCC-UHFFFAOYSA-N 7-methyl-2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CSC1=NC=CC(C=2N3C=CC(C)=CC3=NC=2C=2N=C(C)C=CC=2)=N1 PJCQKRMVXDOQCC-UHFFFAOYSA-N 0.000 description 2
• FQPQPRZYKJLJIA-UHFFFAOYSA-N 7-methyl-2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound N1=C2C=C(C)C=CN2C(C=2N=C(N=CC=2)S(C)(=O)=O)=C1C1=CC=CC(C)=N1 FQPQPRZYKJLJIA-UHFFFAOYSA-N 0.000 description 2
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 2
• VTCFAEGIUJRJNF-UHFFFAOYSA-N 8-methyl-2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=C(C)C3=N2)C=2N=C(N=CC=2)S(C)(=O)=O)=N1 VTCFAEGIUJRJNF-UHFFFAOYSA-N 0.000 description 2
• 239000005695 Ammonium acetate Substances 0.000 description 2
• 108010005853 Anti-Mullerian Hormone Proteins 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• 102000007350 Bone Morphogenetic Proteins Human genes 0.000 description 2
• 108010007726 Bone Morphogenetic Proteins Proteins 0.000 description 2
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
• 229930182816 L-glutamine Natural products 0.000 description 2
• 241000270322 Lepidosauria Species 0.000 description 2
• 241001465754 Metazoa Species 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• 102100025725 Mothers against decapentaplegic homolog 4 Human genes 0.000 description 2
• 101710143112 Mothers against decapentaplegic homolog 4 Proteins 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 108091000080 Phosphotransferase Proteins 0.000 description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
• 239000007868 Raney catalyst Substances 0.000 description 2
• 229910000564 Raney nickel Inorganic materials 0.000 description 2
• 108091005682 Receptor kinases Proteins 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• 230000003213 activating effect Effects 0.000 description 2
• 230000004913 activation Effects 0.000 description 2
• 229910021529 ammonia Inorganic materials 0.000 description 2
• 235000019257 ammonium acetate Nutrition 0.000 description 2
• 229940043376 ammonium acetate Drugs 0.000 description 2
• 235000012538 ammonium bicarbonate Nutrition 0.000 description 2
• 239000000868 anti-mullerian hormone Substances 0.000 description 2
• 239000012131 assay buffer Substances 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• 125000002619 bicyclic group Chemical group 0.000 description 2
• 230000004071 biological effect Effects 0.000 description 2
• 229940112869 bone morphogenetic protein Drugs 0.000 description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
• 238000004113 cell culture Methods 0.000 description 2
• 125000001309 chloro group Chemical group Cl* 0.000 description 2
• 235000015165 citric acid Nutrition 0.000 description 2
• 239000013058 crude material Substances 0.000 description 2
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
• 230000001086 cytosolic effect Effects 0.000 description 2
• 230000003013 cytotoxicity Effects 0.000 description 2
• 231100000135 cytotoxicity Toxicity 0.000 description 2
• 230000008021 deposition Effects 0.000 description 2
• 230000004069 differentiation Effects 0.000 description 2
• 239000012894 fetal calf serum Substances 0.000 description 2
• 239000012458 free base Substances 0.000 description 2
• 239000007789 gas Substances 0.000 description 2
• XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 2
• 208000013403 hyperactivity Diseases 0.000 description 2
• 238000011534 incubation Methods 0.000 description 2
• 210000004969 inflammatory cell Anatomy 0.000 description 2
• 230000028709 inflammatory response Effects 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• 230000003993 interaction Effects 0.000 description 2
• 230000003834 intracellular effect Effects 0.000 description 2
• 229910052740 iodine Inorganic materials 0.000 description 2
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 108020004999 messenger RNA Proteins 0.000 description 2
• MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 description 2
• 210000000651 myofibroblast Anatomy 0.000 description 2
• OYNAFVDEMSUPFN-UHFFFAOYSA-N n'-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]butane-1,4-diamine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCCN)N=CC=2)=N1 OYNAFVDEMSUPFN-UHFFFAOYSA-N 0.000 description 2
• UVHPZRONHYJPKH-UHFFFAOYSA-N n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]pyridine-3-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(NC(=O)C=4C=NC=CC=4)=NC3=N2)C=2N=C(N=CC=2)S(C)(=O)=O)=N1 UVHPZRONHYJPKH-UHFFFAOYSA-N 0.000 description 2
• 229910052759 nickel Inorganic materials 0.000 description 2
• 210000000056 organ Anatomy 0.000 description 2
• 239000012044 organic layer Substances 0.000 description 2
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
• 102000020233 phosphotransferase Human genes 0.000 description 2
• 125000003386 piperidinyl group Chemical group 0.000 description 2
• 102000054765 polymorphisms of proteins Human genes 0.000 description 2
• IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 108090000765 processed proteins & peptides Proteins 0.000 description 2
• RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
• 125000006239 protecting group Chemical group 0.000 description 2
• 238000000746 purification Methods 0.000 description 2
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 2
• IIHQNAXFIODVDU-UHFFFAOYSA-N pyrimidine-2-carbonitrile Chemical compound N#CC1=NC=CC=N1 IIHQNAXFIODVDU-UHFFFAOYSA-N 0.000 description 2
• 230000005855 radiation Effects 0.000 description 2
• 230000009467 reduction Effects 0.000 description 2
• 229910052702 rhenium Inorganic materials 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 229920006395 saturated elastomer Polymers 0.000 description 2
• 230000007781 signaling event Effects 0.000 description 2
• 150000003385 sodium Chemical class 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 2
• 229940054269 sodium pyruvate Drugs 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
• 210000002536 stromal cell Anatomy 0.000 description 2
• 125000001544 thienyl group Chemical group 0.000 description 2
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 230000035897 transcription Effects 0.000 description 2
• 238000013518 transcription Methods 0.000 description 2
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
• TXPRFSOGPYITOT-UHFFFAOYSA-N (6-aminopyridin-3-yl)methanol Chemical compound NC1=CC=C(CO)C=N1 TXPRFSOGPYITOT-UHFFFAOYSA-N 0.000 description 1
• IDFPQEHZYBXIFO-GFCCVEGCSA-N (R)-(4-fluoro-2-propylphenyl)-(1H-imidazol-2-yl)methanol Chemical compound CCCc1cc(F)ccc1[C@@H](O)c1ncc[nH]1 IDFPQEHZYBXIFO-GFCCVEGCSA-N 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
• GFPKJHASUZCPRI-UHFFFAOYSA-N 1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.CC(=O)C1=CC=CN=C1 GFPKJHASUZCPRI-UHFFFAOYSA-N 0.000 description 1
• WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 1
• YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
• UPEWDRCXLROYOF-UHFFFAOYSA-N 2-(2-methoxyphenyl)acetyl chloride Chemical compound COC1=CC=CC=C1CC(Cl)=O UPEWDRCXLROYOF-UHFFFAOYSA-N 0.000 description 1
• ZCAQUEDEXNUXRD-UHFFFAOYSA-N 2-(3-methoxyphenyl)-n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]acetamide Chemical compound COC1=CC=CC(CC(=O)NC2=NC3=NC(=C(N3C=C2)C=2N=C(SC)N=CC=2)C=2N=C(C)C=CC=2)=C1 ZCAQUEDEXNUXRD-UHFFFAOYSA-N 0.000 description 1
• UZUYKYNVSJTWEH-UHFFFAOYSA-N 2-(3-methoxyphenyl)acetyl chloride Chemical compound COC1=CC=CC(CC(Cl)=O)=C1 UZUYKYNVSJTWEH-UHFFFAOYSA-N 0.000 description 1
• VLMLWTYXXPEMQA-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(=N1)C=1N=C2N(C=CC=C2)C=1 VLMLWTYXXPEMQA-UHFFFAOYSA-N 0.000 description 1
• OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 description 1
• IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 1
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
• ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000006040 2-hexenyl group Chemical group 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• GMTUMMOHQBYCFG-UHFFFAOYSA-N 2-pyridin-3-ylpropanamide Chemical compound NC(=O)C(C)C1=CC=CN=C1 GMTUMMOHQBYCFG-UHFFFAOYSA-N 0.000 description 1
• BUTKIHRNYUEGKB-UHFFFAOYSA-N 3,3-dimethylbutanoyl chloride Chemical compound CC(C)(C)CC(Cl)=O BUTKIHRNYUEGKB-UHFFFAOYSA-N 0.000 description 1
• YUPNYCFIICXNPO-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)-n-methylsulfonylimidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NS(C)(=O)=O)C=2N=C(N)N=CC=2)=N1 YUPNYCFIICXNPO-UHFFFAOYSA-N 0.000 description 1
• CLIRYVSLRLIRFS-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C(N)=O)C=2N=C(N)N=CC=2)=N1 CLIRYVSLRLIRFS-UHFFFAOYSA-N 0.000 description 1
• VJJLFUGNAPGFAM-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-N-hydroxy-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C(=O)NO)C=2N=C(N)N=CC=2)=N1 VJJLFUGNAPGFAM-UHFFFAOYSA-N 0.000 description 1
• IHBLACKKNNTMNA-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-[3-(4-methylpiperazin-1-yl)propyl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound C1CN(C)CCN1CCCNC(=O)C1=CN2C(C=3N=C(N)N=CC=3)=C(C=3N=C(C)C=CC=3)N=C2C=C1 IHBLACKKNNTMNA-UHFFFAOYSA-N 0.000 description 1
• KEVVIUGJRUOWCB-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-cyclopropyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NC2CC2)C=2N=C(N)N=CC=2)=N1 KEVVIUGJRUOWCB-UHFFFAOYSA-N 0.000 description 1
• WNOGQPVYYPDYIN-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-ethyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NCC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 WNOGQPVYYPDYIN-UHFFFAOYSA-N 0.000 description 1
• WDGXIUUWINKTGP-UHFFFAOYSA-N 3-(3-pyridinyl)propanoic acid Chemical compound OC(=O)CCC1=CC=CN=C1 WDGXIUUWINKTGP-UHFFFAOYSA-N 0.000 description 1
• RGUABPVONIGVAT-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propan-1-amine Chemical compound CN1CCN(CCCN)CC1 RGUABPVONIGVAT-UHFFFAOYSA-N 0.000 description 1
• CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
• 229940018563 3-aminophenol Drugs 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• RGDQRXPEZUNWHX-UHFFFAOYSA-N 3-methylpyridin-2-amine Chemical compound CC1=CC=CN=C1N RGDQRXPEZUNWHX-UHFFFAOYSA-N 0.000 description 1
• XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
• FXNSVEQMUYPYJS-UHFFFAOYSA-N 4-(2-aminoethyl)benzenesulfonamide Chemical compound NCCC1=CC=C(S(N)(=O)=O)C=C1 FXNSVEQMUYPYJS-UHFFFAOYSA-N 0.000 description 1
• BFWYZZPDZZGSLJ-UHFFFAOYSA-N 4-(aminomethyl)aniline Chemical compound NCC1=CC=C(N)C=C1 BFWYZZPDZZGSLJ-UHFFFAOYSA-N 0.000 description 1
• MGGVALXERJRIRO-UHFFFAOYSA-N 4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-2-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-1H-pyrazol-5-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)O MGGVALXERJRIRO-UHFFFAOYSA-N 0.000 description 1
• WNHKNNXDZWKEPX-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(2h-tetrazol-5-yl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NC=3NN=NN=3)N=CC=2)=N1 WNHKNNXDZWKEPX-UHFFFAOYSA-N 0.000 description 1
• ATHLSRWZRBEENC-UHFFFAOYSA-N 4-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]morpholine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)N2CCOCC2)=N1 ATHLSRWZRBEENC-UHFFFAOYSA-N 0.000 description 1
• ZYRJAHHKBMBPCR-UHFFFAOYSA-N 4-[6-methyl-2-(6-methylpyridin-2-yl)-8-morpholin-4-ylimidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C12=NC(C=3N=C(C)C=CC=3)=C(C=3N=C(N)N=CC=3)N2C=C(C)C=C1N1CCOCC1 ZYRJAHHKBMBPCR-UHFFFAOYSA-N 0.000 description 1
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
• KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
• PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 description 1
• RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
• GYMNCTNUNURQSP-UHFFFAOYSA-N 4-methyl-2,6-bis(methylsulfanyl)pyrimidine Chemical compound CSC1=CC(C)=NC(SC)=N1 GYMNCTNUNURQSP-UHFFFAOYSA-N 0.000 description 1
• ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 description 1
• 125000004608 5,6,7,8-tetrahydroquinolinyl group Chemical group N1=C(C=CC=2CCCCC12)* 0.000 description 1
• ZLZCRVQDMUKNHC-UHFFFAOYSA-N 5-(dimethylamino)-n-[4-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]butyl]naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NCCCCNC(N=1)=NC=CC=1C(N1C=CC=CC1=N1)=C1C1=CC=CC(C)=N1 ZLZCRVQDMUKNHC-UHFFFAOYSA-N 0.000 description 1
• MBBZMMPHUWSWHV-UHFFFAOYSA-N 6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound CNCC(O)C(O)C(O)C(O)CO MBBZMMPHUWSWHV-UHFFFAOYSA-N 0.000 description 1
• SKOKDMSZJTZWIE-UHFFFAOYSA-N 6-[6-methyl-2-(6-methylpyridin-2-yl)-8-(2-morpholin-4-ylethylamino)imidazo[1,2-a]pyridin-3-yl]-1h-pyrimidin-2-one Chemical compound C12=NC(C=3N=C(C)C=CC=3)=C(C=3N=C(O)N=CC=3)N2C=C(C)C=C1NCCN1CCOCC1 SKOKDMSZJTZWIE-UHFFFAOYSA-N 0.000 description 1
• OGXNGNBWPQBARQ-UHFFFAOYSA-N 6-[6-methyl-2-(6-methylpyridin-2-yl)-8-morpholin-4-ylimidazo[1,2-a]pyridin-3-yl]-1h-pyrimidin-2-one Chemical compound C12=NC(C=3N=C(C)C=CC=3)=C(C=3N=C(O)N=CC=3)N2C=C(C)C=C1N1CCOCC1 OGXNGNBWPQBARQ-UHFFFAOYSA-N 0.000 description 1
• LBCXQVLCSXLIMW-UHFFFAOYSA-N 6-chloro-2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CSC1=NC=CC(C=2N3C=C(Cl)C=CC3=NC=2C=2N=C(C)C=CC=2)=N1 LBCXQVLCSXLIMW-UHFFFAOYSA-N 0.000 description 1
• UQJLPBLXSJWAKG-UHFFFAOYSA-N 6-methyl-1h-pyrimidin-3-ium-2-thione;chloride Chemical compound Cl.CC1=CC=NC(=S)N1 UQJLPBLXSJWAKG-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• VRTPXELPGWYACN-UHFFFAOYSA-N 8-methyl-2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CSC1=NC=CC(C=2N3C=CC=C(C)C3=NC=2C=2N=C(C)C=CC=2)=N1 VRTPXELPGWYACN-UHFFFAOYSA-N 0.000 description 1
• JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 description 1
• PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
• GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
• 239000005541 ACE inhibitor Substances 0.000 description 1
• 102100034111 Activin receptor type-1 Human genes 0.000 description 1
• 101710105225 Activin receptor type-1 Proteins 0.000 description 1
• RYVZYACBVYKUHD-UHFFFAOYSA-N Alk5 Natural products CC#CC#CCCCCC=CC(=O)NCC(C)C RYVZYACBVYKUHD-UHFFFAOYSA-N 0.000 description 1
• 108010006654 Bleomycin Proteins 0.000 description 1
• 241000283690 Bos taurus Species 0.000 description 1
• JIRIQGZUUBTROM-UHFFFAOYSA-N Br.ClC=1C=CC=2N(C1)C(=C(N2)C2=NC(=CC=C2)C)C2=NC(=NC=C2)SC Chemical compound Br.ClC=1C=CC=2N(C1)C(=C(N2)C2=NC(=CC=C2)C)C2=NC(=NC=C2)SC JIRIQGZUUBTROM-UHFFFAOYSA-N 0.000 description 1
• 206010006187 Breast cancer Diseases 0.000 description 1
• 208000026310 Breast neoplasm Diseases 0.000 description 1
• VMLBQGNOWVIXMX-UHFFFAOYSA-N CC1=NC(=CC=C1)C2=C(N3C=CC=CC3=N2)C4=NC(=NC=C4)NCCCCNC(=O)CSC5=CC=CC=C5C(=O)O Chemical compound CC1=NC(=CC=C1)C2=C(N3C=CC=CC3=N2)C4=NC(=NC=C4)NCCCCNC(=O)CSC5=CC=CC=C5C(=O)O VMLBQGNOWVIXMX-UHFFFAOYSA-N 0.000 description 1
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• 241000283707 Capra Species 0.000 description 1
• 241000700199 Cavia porcellus Species 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 201000000054 Coronary Restenosis Diseases 0.000 description 1
• 206010056489 Coronary artery restenosis Diseases 0.000 description 1
• 241000699800 Cricetinae Species 0.000 description 1
• 229920000858 Cyclodextrin Polymers 0.000 description 1
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
• 241000283073 Equus caballus Species 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• 102000016359 Fibronectins Human genes 0.000 description 1
• 108010067306 Fibronectins Proteins 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 241000699694 Gerbillinae Species 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• 239000004471 Glycine Substances 0.000 description 1
• 229910004373 HOAc Inorganic materials 0.000 description 1
• 241000238631 Hexapoda Species 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
• 101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 1
• 201000003838 Idiopathic interstitial pneumonia Diseases 0.000 description 1
• 206010062016 Immunosuppression Diseases 0.000 description 1
• 208000020060 Increased inflammatory response Diseases 0.000 description 1
• 206010061216 Infarction Diseases 0.000 description 1
• 108010004250 Inhibins Proteins 0.000 description 1
• 102000002746 Inhibins Human genes 0.000 description 1
• OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
• 101710128836 Large T antigen Proteins 0.000 description 1
• 101800001155 Latency-associated peptide Proteins 0.000 description 1
• 108060001084 Luciferase Proteins 0.000 description 1
• 241000699666 Mus <mouse, genus> Species 0.000 description 1
• 241000699660 Mus musculus Species 0.000 description 1
• 241000282341 Mustela putorius furo Species 0.000 description 1
• AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
• XFPHNCLVPRONFC-UHFFFAOYSA-N NCCNC(C1=CC2=NC=CN2C=C1)=O Chemical compound NCCNC(C1=CC2=NC=CN2C=C1)=O XFPHNCLVPRONFC-UHFFFAOYSA-N 0.000 description 1
• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
• 206010053159 Organ failure Diseases 0.000 description 1
• 241000283973 Oryctolagus cuniculus Species 0.000 description 1
• 101150003085 Pdcl gene Proteins 0.000 description 1
• 241001494479 Pecora Species 0.000 description 1
• 229930182555 Penicillin Natural products 0.000 description 1
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
• 206010034665 Peritoneal fibrosis Diseases 0.000 description 1
• 241000009328 Perro Species 0.000 description 1
• BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 229910052774 Proactinium Inorganic materials 0.000 description 1
• 102000001253 Protein Kinase Human genes 0.000 description 1
• 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 description 1
• 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 description 1
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
• 241000700159 Rattus Species 0.000 description 1
• 101100437153 Rattus norvegicus Acvr2b gene Proteins 0.000 description 1
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
• 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 1
• 101100289792 Squirrel monkey polyomavirus large T gene Proteins 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 241000282898 Sus scrofa Species 0.000 description 1
• 238000006069 Suzuki reaction reaction Methods 0.000 description 1
• 102000007614 Thrombospondin 1 Human genes 0.000 description 1
• 108010046722 Thrombospondin 1 Proteins 0.000 description 1
• 208000031737 Tissue Adhesions Diseases 0.000 description 1
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
• 102100029645 UBX domain-containing protein 11 Human genes 0.000 description 1
• 208000012346 Venoocclusive disease Diseases 0.000 description 1
• KYWGAKUZLDKVDY-UHFFFAOYSA-N [2-(6-methylpyridin-2-yl)-3-pyrimidin-4-ylimidazo[1,2-a]pyridin-7-yl]methanamine Chemical compound CC1=CC=CC(C2=C(N3C=CC(CN)=CC3=N2)C=2N=CN=CC=2)=N1 KYWGAKUZLDKVDY-UHFFFAOYSA-N 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 150000003973 alkyl amines Chemical class 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 238000005576 amination reaction Methods 0.000 description 1
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
• 229940121363 anti-inflammatory agent Drugs 0.000 description 1
• 239000002260 anti-inflammatory agent Substances 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 230000001363 autoimmune Effects 0.000 description 1
• 239000003637 basic solution Substances 0.000 description 1
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• 230000033228 biological regulation Effects 0.000 description 1
• 239000000090 biomarker Substances 0.000 description 1
• 229960001561 bleomycin Drugs 0.000 description 1
• OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
• 210000004899 c-terminal region Anatomy 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
• 125000002837 carbocyclic group Chemical group 0.000 description 1
• 229910052799 carbon Inorganic materials 0.000 description 1
• 229910002091 carbon monoxide Inorganic materials 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 230000025084 cell cycle arrest Effects 0.000 description 1
• 230000024245 cell differentiation Effects 0.000 description 1
• 230000006041 cell recruitment Effects 0.000 description 1
• 230000003833 cell viability Effects 0.000 description 1
• 238000012200 cell viability kit Methods 0.000 description 1
• 230000033077 cellular process Effects 0.000 description 1
• KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 208000017760 chronic graft versus host disease Diseases 0.000 description 1
• 230000007882 cirrhosis Effects 0.000 description 1
• 238000003776 cleavage reaction Methods 0.000 description 1
• 230000002596 correlated effect Effects 0.000 description 1
• 230000000875 corresponding effect Effects 0.000 description 1
• 229940097362 cyclodextrins Drugs 0.000 description 1
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
• NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 238000001212 derivatisation Methods 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 230000018109 developmental process Effects 0.000 description 1
• 238000000502 dialysis Methods 0.000 description 1
• 235000015872 dietary supplement Nutrition 0.000 description 1
• 125000005879 dioxolanyl group Chemical group 0.000 description 1
• 230000007783 downstream signaling Effects 0.000 description 1
• 239000003221 ear drop Substances 0.000 description 1
• 229940047652 ear drops Drugs 0.000 description 1
• 150000002085 enols Chemical class 0.000 description 1
• 210000002919 epithelial cell Anatomy 0.000 description 1
• 239000003797 essential amino acid Substances 0.000 description 1
• 235000020776 essential amino acid Nutrition 0.000 description 1
• 230000032050 esterification Effects 0.000 description 1
• 238000005886 esterification reaction Methods 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 description 1
• XVBZFXZNJAFCHL-UHFFFAOYSA-N ethyl 2-aminopyridine-4-carboxylate Chemical compound CCOC(=O)C1=CC=NC(N)=C1 XVBZFXZNJAFCHL-UHFFFAOYSA-N 0.000 description 1
• FMSXHQBTRLUYHP-UHFFFAOYSA-N ethyl 6-methylpyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=CC(C)=N1 FMSXHQBTRLUYHP-UHFFFAOYSA-N 0.000 description 1
• PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
• 230000005284 excitation Effects 0.000 description 1
• 230000029142 excretion Effects 0.000 description 1
• 239000003889 eye drop Substances 0.000 description 1
• 229940012356 eye drops Drugs 0.000 description 1
• 150000004665 fatty acids Chemical group 0.000 description 1
• 210000002950 fibroblast Anatomy 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 230000037406 food intake Effects 0.000 description 1
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
• 125000004967 formylalkyl group Chemical group 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 235000011087 fumaric acid Nutrition 0.000 description 1
• 229960002598 fumaric acid Drugs 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 230000012010 growth Effects 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 125000004438 haloalkoxy group Chemical group 0.000 description 1
• 229910052736 halogen Inorganic materials 0.000 description 1
• 150000002367 halogens Chemical class 0.000 description 1
• 210000003958 hematopoietic stem cell Anatomy 0.000 description 1
• 125000000623 heterocyclic group Chemical group 0.000 description 1
• 235000003642 hunger Nutrition 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• 229940071870 hydroiodic acid Drugs 0.000 description 1
• XPGRZDJXVKFLHQ-UHFFFAOYSA-N hydron;methyl 3-aminopropanoate;chloride Chemical compound Cl.COC(=O)CCN XPGRZDJXVKFLHQ-UHFFFAOYSA-N 0.000 description 1
• MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
• 230000033444 hydroxylation Effects 0.000 description 1
• 238000005805 hydroxylation reaction Methods 0.000 description 1
• BOJQXJHNUIWISM-UHFFFAOYSA-N imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C(N)C=CN2C=CN=C21 BOJQXJHNUIWISM-UHFFFAOYSA-N 0.000 description 1
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
• 210000000987 immune system Anatomy 0.000 description 1
• 230000001506 immunosuppresive effect Effects 0.000 description 1
• 238000002513 implantation Methods 0.000 description 1
• 239000012535 impurity Substances 0.000 description 1
• 238000010348 incorporation Methods 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• 229910052738 indium Inorganic materials 0.000 description 1
• LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 230000002757 inflammatory effect Effects 0.000 description 1
• 239000000893 inhibin Substances 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 150000002576 ketones Chemical group 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 238000002684 laminectomy Methods 0.000 description 1
• 239000010410 layer Substances 0.000 description 1
• QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 239000012669 liquid formulation Substances 0.000 description 1
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
• 238000011866 long-term treatment Methods 0.000 description 1
• 238000003468 luciferase reporter gene assay Methods 0.000 description 1
• 210000004324 lymphatic system Anatomy 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 229940098895 maleic acid Drugs 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 229940099690 malic acid Drugs 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 230000010534 mechanism of action Effects 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• 230000009681 mesenchymal cell proliferation Effects 0.000 description 1
• 230000004060 metabolic process Effects 0.000 description 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
• VVALHDDBBJJYDI-UHFFFAOYSA-N methyl 3-[[3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carbonyl]amino]propanoate Chemical compound N12C=C(C(=O)NCCC(=O)OC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 VVALHDDBBJJYDI-UHFFFAOYSA-N 0.000 description 1
• UZCXPYDBYUEZCV-UHFFFAOYSA-N methyl 3-aminopropanoate Chemical compound COC(=O)CCN UZCXPYDBYUEZCV-UHFFFAOYSA-N 0.000 description 1
• JACPDLJUQLKABC-UHFFFAOYSA-N methyl 6-aminopyridine-3-carboxylate Chemical compound COC(=O)C1=CC=C(N)N=C1 JACPDLJUQLKABC-UHFFFAOYSA-N 0.000 description 1
• 230000005012 migration Effects 0.000 description 1
• 238000013508 migration Methods 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 238000000329 molecular dynamics simulation Methods 0.000 description 1
• 125000002950 monocyclic group Chemical group 0.000 description 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
• 125000002757 morpholinyl group Chemical group 0.000 description 1
• 206010028537 myelofibrosis Diseases 0.000 description 1
• OXHZBUYAJNKADR-UHFFFAOYSA-N n'-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]propane-1,3-diamine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCN)N=CC=2)=N1 OXHZBUYAJNKADR-UHFFFAOYSA-N 0.000 description 1
• DAKZISABEDGGSV-UHFFFAOYSA-N n-(2-aminoethyl)acetamide Chemical compound CC(=O)NCCN DAKZISABEDGGSV-UHFFFAOYSA-N 0.000 description 1
• CERYWFBSRQOQIA-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(OC)=CC=C1CNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 CERYWFBSRQOQIA-UHFFFAOYSA-N 0.000 description 1
• IFYDWYVPVAMGRO-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]tetradecanamide Chemical compound CCCCCCCCCCCCCC(=O)NCCCN(C)C IFYDWYVPVAMGRO-UHFFFAOYSA-N 0.000 description 1
• WZEQZQOEXMACDP-UHFFFAOYSA-N n-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]-1,3,4-thiadiazol-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NC=3SC=NN=3)N=CC=2)=N1 WZEQZQOEXMACDP-UHFFFAOYSA-N 0.000 description 1
• BOZKLPKKXYBXKP-UHFFFAOYSA-N n-cyclopropyl-n-methyl-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound N=1C=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=NC=1N(C)C1CC1 BOZKLPKKXYBXKP-UHFFFAOYSA-N 0.000 description 1
• JNHZPXFARRJZQR-UHFFFAOYSA-N n-ethylpyridin-3-amine Chemical compound CCNC1=CC=CN=C1 JNHZPXFARRJZQR-UHFFFAOYSA-N 0.000 description 1
• OTIDWUALRXXVIM-UHFFFAOYSA-N n-ethylpyridin-4-amine Chemical compound CCNC1=CC=NC=C1 OTIDWUALRXXVIM-UHFFFAOYSA-N 0.000 description 1
• 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• UENXTWNHCJUNJJ-UHFFFAOYSA-N n-methyl-1,4-dioxan-2-amine Chemical compound CNC1COCCO1 UENXTWNHCJUNJJ-UHFFFAOYSA-N 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• YLQBPWQRPIJFPO-UHFFFAOYSA-N n-propylimidazol-1-amine Chemical compound CCCNN1C=CN=C1 YLQBPWQRPIJFPO-UHFFFAOYSA-N 0.000 description 1
• JXKAILMMPPFNOX-UHFFFAOYSA-N n-propylmorpholin-3-amine Chemical compound CCCNC1COCCN1 JXKAILMMPPFNOX-UHFFFAOYSA-N 0.000 description 1
• 210000004897 n-terminal region Anatomy 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 230000007935 neutral effect Effects 0.000 description 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
• 125000006574 non-aromatic ring group Chemical group 0.000 description 1
• 230000009871 nonspecific binding Effects 0.000 description 1
• 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
• 125000005889 octahydrochromenyl group Chemical group 0.000 description 1
• 125000005060 octahydroindolyl group Chemical group N1(CCC2CCCCC12)* 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 125000000160 oxazolidinyl group Chemical group 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• 230000035515 penetration Effects 0.000 description 1
• 229940049954 penicillin Drugs 0.000 description 1
• 239000012071 phase Substances 0.000 description 1
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
• 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
• 229950000688 phenothiazine Drugs 0.000 description 1
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• 229960004838 phosphoric acid Drugs 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
• 229940012957 plasmin Drugs 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 229920002704 polyhistidine Polymers 0.000 description 1
• 229920001184 polypeptide Polymers 0.000 description 1
• 230000026341 positive regulation of angiogenesis Effects 0.000 description 1
• 230000030795 positive regulation of cellular component movement Effects 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 239000002243 precursor Substances 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 230000003449 preventive effect Effects 0.000 description 1
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 230000002062 proliferating effect Effects 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 1
• HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
• YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 description 1
• ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 230000007017 scission Effects 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 230000028327 secretion Effects 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 239000000377 silicon dioxide Substances 0.000 description 1
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
• 150000003384 small molecules Chemical class 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
• 230000003381 solubilizing effect Effects 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 230000037351 starvation Effects 0.000 description 1
• 150000003431 steroids Chemical class 0.000 description 1
• 230000000638 stimulation Effects 0.000 description 1
• 229960005322 streptomycin Drugs 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
• 229910052717 sulfur Inorganic materials 0.000 description 1
• 229940032330 sulfuric acid Drugs 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 230000001629 suppression Effects 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• AOCSUUGBCMTKJH-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCN AOCSUUGBCMTKJH-UHFFFAOYSA-N 0.000 description 1
• POHWAQLZBIMPRN-UHFFFAOYSA-N tert-butyl n-(3-aminopropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCN POHWAQLZBIMPRN-UHFFFAOYSA-N 0.000 description 1
• ZFQWJXFJJZUVPI-UHFFFAOYSA-N tert-butyl n-(4-aminobutyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCCN ZFQWJXFJJZUVPI-UHFFFAOYSA-N 0.000 description 1
• DPLOGSUBQDREOU-UHFFFAOYSA-N tert-butyl n-(5-aminopentyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCN DPLOGSUBQDREOU-UHFFFAOYSA-N 0.000 description 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 238000011830 transgenic mouse model Methods 0.000 description 1
• LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 description 1
• XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Natural products NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
• 241000701447 unidentified baculovirus Species 0.000 description 1