JP2016500073A5

JP2016500073A5 -

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Publication number: JP2016500073A5
Authority: JP; Japan
Prior art keywords: carboxamide; pyrazine; methyl; imidazo; phenyl
Prior art date: 2013-11-18
Legal status : Pending

Application number

JP2015543098A

Other languages

English (en)

Japanese (ja)

Other versions

JP2016500073A (ja

Filing date

2013-11-18

Publication date

2016-12-28

2013-11-18 Application filed filed Critical

2013-11-18 Priority claimed from PCT/US2013/070623 external-priority patent/WO2014078813A1/en

2016-01-07 Publication of JP2016500073A publication Critical patent/JP2016500073A/ja

2016-12-28 Publication of JP2016500073A5 publication Critical patent/JP2016500073A5/ja

Status Pending legal-status Critical Current

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-1 alkyl R 10 Chemical compound 0.000 claims 63
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 36
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 35
125000000217 alkyl group Chemical group 0.000 claims 35
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 14
125000000592 heterocycloalkyl group Chemical group 0.000 claims 12
125000001424 substituent group Chemical group 0.000 claims 12
229910052739 hydrogen Inorganic materials 0.000 claims 11
239000001257 hydrogen Substances 0.000 claims 11
150000001875 compounds Chemical class 0.000 claims 9
125000001072 heteroaryl group Chemical group 0.000 claims 9
125000003545 alkoxy group Chemical group 0.000 claims 8
125000003282 alkyl amino group Chemical group 0.000 claims 8
150000003857 carboxamides Chemical class 0.000 claims 8
125000005843 halogen group Chemical group 0.000 claims 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
229910052799 carbon Inorganic materials 0.000 claims 7
150000002431 hydrogen Chemical class 0.000 claims 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 6
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 5
125000003368 amide group Chemical group 0.000 claims 5
125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
125000004093 cyano group Chemical group *C#N 0.000 claims 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims 4
125000002947 alkylene group Chemical group 0.000 claims 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
125000000753 cycloalkyl group Chemical group 0.000 claims 3
239000003814 drug Substances 0.000 claims 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 2
125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
MTXFOVIHTGSHPJ-UHFFFAOYSA-N 4-chloro-n-methyl-n-[[3-(4-pyrazol-1-ylphenyl)imidazo[1,2-a]pyrazin-6-yl]methyl]aniline Chemical compound C=1C=C(Cl)C=CC=1N(C)CC(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1N1C=CC=N1 MTXFOVIHTGSHPJ-UHFFFAOYSA-N 0.000 claims 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims 2
239000003430 antimalarial agent Substances 0.000 claims 2
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
229940079593 drug Drugs 0.000 claims 2
125000001153 fluoro group Chemical group F* 0.000 claims 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims 2
ZKHBYXUVKJJTFQ-UHFFFAOYSA-N n-(2-methoxy-5-methylpyridin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound COC1=NC=C(C)C=C1N(C)C(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 ZKHBYXUVKJJTFQ-UHFFFAOYSA-N 0.000 claims 2
HAAOTCNYMJXNBN-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(furan-2-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=CO1 HAAOTCNYMJXNBN-UHFFFAOYSA-N 0.000 claims 2
YOLQYBRDVZJFEO-UHFFFAOYSA-N n-(6-cyanopyridin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 YOLQYBRDVZJFEO-UHFFFAOYSA-N 0.000 claims 2
PAAICFBDMKXDIW-UHFFFAOYSA-N n-methyl-3-[4-(trifluoromethyl)phenyl]-n-[5-(trifluoromethyl)pyridin-2-yl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 PAAICFBDMKXDIW-UHFFFAOYSA-N 0.000 claims 2
HHPIVZLMDVERHJ-UHFFFAOYSA-N n-methyl-n-(5-methylpyrazin-2-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N=C(C)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 HHPIVZLMDVERHJ-UHFFFAOYSA-N 0.000 claims 2
125000004043 oxo group Chemical group O=* 0.000 claims 2
125000004076 pyridyl group Chemical group 0.000 claims 2
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 claims 2
150000003839 salts Chemical class 0.000 claims 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
XEEQGYMUWCZPDN-DOMZBBRYSA-N (-)-(11S,2'R)-erythro-mefloquine Chemical compound C([C@@H]1[C@@H](O)C=2C3=CC=CC(=C3N=C(C=2)C(F)(F)F)C(F)(F)F)CCCN1 XEEQGYMUWCZPDN-DOMZBBRYSA-N 0.000 claims 1
XDEHMKQLKPZERH-SCSAIBSYSA-N (2r)-2-amino-3-methylbutanamide Chemical compound CC(C)[C@@H](N)C(N)=O XDEHMKQLKPZERH-SCSAIBSYSA-N 0.000 claims 1
SNZTWUZDBJSYBL-RZVRUWJTSA-N (2s)-2-amino-3-methylbutanamide Chemical compound CC(C)[C@H](N)C(N)=O.CC(C)[C@H](N)C(N)=O SNZTWUZDBJSYBL-RZVRUWJTSA-N 0.000 claims 1
OTVXVVYHNZUDSN-GSVOUGTGSA-N (3r)-3-aminobutanamide Chemical compound C[C@@H](N)CC(N)=O OTVXVVYHNZUDSN-GSVOUGTGSA-N 0.000 claims 1
SVDDNCKPGUGLAG-YFKPBYRVSA-N (3s)-3-amino-4-methylpentanamide Chemical compound CC(C)[C@@H](N)CC(N)=O SVDDNCKPGUGLAG-YFKPBYRVSA-N 0.000 claims 1
YPEJEOFUCARJEY-UHFFFAOYSA-N (5-fluoro-2,3-dihydroindol-1-yl)-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methanone Chemical compound C1CC2=CC(F)=CC=C2N1C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 YPEJEOFUCARJEY-UHFFFAOYSA-N 0.000 claims 1
RZTQEFJMOVODAW-UHFFFAOYSA-N (5-methylsulfonyl-2,3-dihydroindol-1-yl)-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methanone Chemical compound C1CC2=CC(S(=O)(=O)C)=CC=C2N1C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 RZTQEFJMOVODAW-UHFFFAOYSA-N 0.000 claims 1
WFDBWAXIIJSYNQ-UHFFFAOYSA-N (6-chloro-3,4-dihydro-2h-quinolin-1-yl)-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CN=C2N1C=C(C(=O)N1C3=CC=C(Cl)C=C3CCC1)N=C2 WFDBWAXIIJSYNQ-UHFFFAOYSA-N 0.000 claims 1
WNJOQELXSUJRGT-UHFFFAOYSA-N (6-fluoro-2,2-dimethyl-3,4-dihydroquinolin-1-yl)-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methanone Chemical compound CC1(C)CCC2=CC(F)=CC=C2N1C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 WNJOQELXSUJRGT-UHFFFAOYSA-N 0.000 claims 1
LFGOQCFQJLGANP-UHFFFAOYSA-N (6-fluoro-3,4-dihydro-2h-quinolin-1-yl)-[3-(2-piperazin-1-ylpyridin-4-yl)imidazo[1,2-a]pyrazin-6-yl]methanone Chemical compound C1CCC2=CC(F)=CC=C2N1C(=O)C(N=CC1=NC=2)=CN1C=2C(C=1)=CC=NC=1N1CCNCC1 LFGOQCFQJLGANP-UHFFFAOYSA-N 0.000 claims 1
MAGDDUSAAOTDCB-UHFFFAOYSA-N (6-fluoro-3,4-dihydro-2h-quinolin-1-yl)-[3-(3-methylsulfonylphenyl)imidazo[1,2-a]pyrazin-6-yl]methanone Chemical compound CS(=O)(=O)C1=CC=CC(C=2N3C=C(N=CC3=NC=2)C(=O)N2C3=CC=C(F)C=C3CCC2)=C1 MAGDDUSAAOTDCB-UHFFFAOYSA-N 0.000 claims 1
RQOZCVSKNPKKIN-UHFFFAOYSA-N (6-fluoro-3,4-dihydro-2h-quinolin-1-yl)-[3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrazin-6-yl]methanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C2N1C=C(C(=O)N1C3=CC=C(F)C=C3CCC1)N=C2 RQOZCVSKNPKKIN-UHFFFAOYSA-N 0.000 claims 1
JNJKPSRVKIQTKU-UHFFFAOYSA-N (6-fluoro-3,4-dihydro-2h-quinolin-1-yl)-[3-[3-(morpholin-4-ylmethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methanone Chemical compound C1CCC2=CC(F)=CC=C2N1C(=O)C(N=CC1=NC=2)=CN1C=2C(C=1)=CC=CC=1CN1CCOCC1 JNJKPSRVKIQTKU-UHFFFAOYSA-N 0.000 claims 1
YTHFVYPUAMGZIP-UHFFFAOYSA-N (6-fluoro-3,4-dihydro-2h-quinolin-1-yl)-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methanone Chemical compound C1CCC2=CC(F)=CC=C2N1C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 YTHFVYPUAMGZIP-UHFFFAOYSA-N 0.000 claims 1
ZMAFHOXTGYVCPP-UHFFFAOYSA-N (6-fluoro-3,4-dihydro-2h-quinolin-1-yl)-[8-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methanone Chemical compound C=1N=C2C(C)=NC(C(=O)N3C4=CC=C(F)C=C4CCC3)=CN2C=1C1=CC=C(C(F)(F)F)C=C1 ZMAFHOXTGYVCPP-UHFFFAOYSA-N 0.000 claims 1
RODDYCFZXNIDRJ-UHFFFAOYSA-N (6-methylsulfonyl-3,4-dihydro-2h-quinolin-1-yl)-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methanone Chemical compound C1CCC2=CC(S(=O)(=O)C)=CC=C2N1C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 RODDYCFZXNIDRJ-UHFFFAOYSA-N 0.000 claims 1
GFCFKQDCROKEGC-UHFFFAOYSA-N (7-fluoro-2,3-dihydro-1,4-benzoxazin-4-yl)-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methanone Chemical compound C1COC2=CC(F)=CC=C2N1C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 GFCFKQDCROKEGC-UHFFFAOYSA-N 0.000 claims 1
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 claims 1
125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims 1
VVOWBFRMVJBOHE-UHFFFAOYSA-N 1-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carbonyl]-3,4-dihydro-2h-quinoline-6-carbonitrile Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CN=C2N1C=C(C(=O)N1C3=CC=C(C=C3CCC1)C#N)N=C2 VVOWBFRMVJBOHE-UHFFFAOYSA-N 0.000 claims 1
OMMNLIHAMIMVOQ-UHFFFAOYSA-N 1-[4-[5-[6-(6-fluoro-3,4-dihydro-2h-quinoline-1-carbonyl)imidazo[1,2-a]pyrazin-3-yl]pyridin-2-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=CC=C(C=2N3C=C(N=CC3=NC=2)C(=O)N2C3=CC=C(F)C=C3CCC2)C=N1 OMMNLIHAMIMVOQ-UHFFFAOYSA-N 0.000 claims 1
DWHWNWNJALLNSW-UHFFFAOYSA-N 1-[[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl]piperidin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CN=C2N1C=C(CN1C(CCCC1)=O)N=C2 DWHWNWNJALLNSW-UHFFFAOYSA-N 0.000 claims 1
ZEGSMFUCRGFAFT-UHFFFAOYSA-N 2,2-dimethyl-4-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carbonyl]-3h-1,4-benzoxazine-7-carbonitrile Chemical compound C12=CC=C(C#N)C=C2OC(C)(C)CN1C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 ZEGSMFUCRGFAFT-UHFFFAOYSA-N 0.000 claims 1
CXWUWMWJXDJKKI-UHFFFAOYSA-N 2-[4-(5-amino-1,3,4-oxadiazol-2-yl)phenyl]-n-(4-chlorophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C(N=CC1=N2)=CN1C=C2C(C=C1)=CC=C1C1=NN=C(N)O1 CXWUWMWJXDJKKI-UHFFFAOYSA-N 0.000 claims 1
UOZTZZCTZFBBGK-UHFFFAOYSA-N 3-(1-benzofuran-5-yl)-n-(6-chloropyridin-3-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=3C=C4C=COC4=CC=3)=CN=C2C=NC=1C(=O)N(C)C1=CC=C(Cl)N=C1 UOZTZZCTZFBBGK-UHFFFAOYSA-N 0.000 claims 1
XHIKNYMHXWQTII-UHFFFAOYSA-N 3-(1-benzylpyrazol-4-yl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(=C1)C=NN1CC1=CC=CC=C1 XHIKNYMHXWQTII-UHFFFAOYSA-N 0.000 claims 1
GPNKVZCLUPVRAC-UHFFFAOYSA-N 3-(1H-indol-2-yl)-N-[6-(1H-indol-2-yl)pyridin-3-yl]-N-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CN(C(=O)c1cn2c(cnc2cn1)-c1cc2ccccc2[nH]1)c1ccc(nc1)-c1cc2ccccc2[nH]1 GPNKVZCLUPVRAC-UHFFFAOYSA-N 0.000 claims 1
GSZZZFUJTWWECP-UHFFFAOYSA-N 3-(2,1,3-benzoxadiazol-5-yl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C3=CC4=NON=C4C=C3)=CN=C2C=NC=1C(=O)N(C)C1=CC=C(C#N)C=C1 GSZZZFUJTWWECP-UHFFFAOYSA-N 0.000 claims 1
LCWXAWBNEMSPKU-UHFFFAOYSA-N 3-(2-aminopyrimidin-5-yl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CN=C(N)N=C1 LCWXAWBNEMSPKU-UHFFFAOYSA-N 0.000 claims 1
JFBRREPYBKHUTH-UHFFFAOYSA-N 3-(2-chloropyridin-4-yl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=NC(Cl)=C1 JFBRREPYBKHUTH-UHFFFAOYSA-N 0.000 claims 1
QTHKZCMNKRYGFY-UHFFFAOYSA-N 3-(3-amino-1h-indazol-5-yl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=3C=C4C(N)=NNC4=CC=3)=CN=C2C=NC=1C(=O)N(C)C1=CC=C(C#N)C=C1 QTHKZCMNKRYGFY-UHFFFAOYSA-N 0.000 claims 1
VGCUFNMBNAKEGW-UHFFFAOYSA-N 3-(3-chloropyridin-2-yl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=NC=CC=C1Cl VGCUFNMBNAKEGW-UHFFFAOYSA-N 0.000 claims 1
SPBDXLUUBSTNQY-UHFFFAOYSA-N 3-(3-cyanophenyl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=CC(C#N)=C1 SPBDXLUUBSTNQY-UHFFFAOYSA-N 0.000 claims 1
CFRFHAPENPURIA-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=3C=C4NC=NC4=CC=3)=CN=C2C=NC=1C(=O)N(C)C1=CC=C(C#N)C=C1 CFRFHAPENPURIA-UHFFFAOYSA-N 0.000 claims 1
ASBPXXJEOCIMLM-UHFFFAOYSA-N 3-(4-acetamidophenyl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(NC(C)=O)C=C1 ASBPXXJEOCIMLM-UHFFFAOYSA-N 0.000 claims 1
QTYWZJQKWHDRCW-UHFFFAOYSA-N 3-(4-acetamidophenyl)-n-(6-chloropyridin-3-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(NC(C)=O)C=C1 QTYWZJQKWHDRCW-UHFFFAOYSA-N 0.000 claims 1
UWIUAXAFERECKZ-UHFFFAOYSA-N 3-(4-acetamidophenyl)-n-methyl-n-(5-methylpyridin-2-yl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(NC(C)=O)C=C1 UWIUAXAFERECKZ-UHFFFAOYSA-N 0.000 claims 1
WBLONGILCSMZCR-UHFFFAOYSA-N 3-(4-acetylphenyl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(C)=O)C=C1 WBLONGILCSMZCR-UHFFFAOYSA-N 0.000 claims 1
SWZXNEJNRWNGEQ-UHFFFAOYSA-N 3-(4-aminophenyl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(N)C=C1 SWZXNEJNRWNGEQ-UHFFFAOYSA-N 0.000 claims 1
JPZOSHHABVAARQ-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(3,4-difluorophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C(F)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(N)=O)C=C1 JPZOSHHABVAARQ-UHFFFAOYSA-N 0.000 claims 1
WQOCLQQTVKCMIW-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(4-chlorophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(N)=O)C=C1 WQOCLQQTVKCMIW-UHFFFAOYSA-N 0.000 claims 1
AAWZTCAMEJBCLP-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(N)=O)C=C1 AAWZTCAMEJBCLP-UHFFFAOYSA-N 0.000 claims 1
RQIBUEJFBWULLL-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(4-fluorophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(N)=O)C=C1 RQIBUEJFBWULLL-UHFFFAOYSA-N 0.000 claims 1
PRZCSQIVJCGTLE-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(6-chloropyridin-3-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(N)=O)C=C1 PRZCSQIVJCGTLE-UHFFFAOYSA-N 0.000 claims 1
MMOFFPDOWHAMBH-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-methyl-n-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(N)=O)C=C1 MMOFFPDOWHAMBH-UHFFFAOYSA-N 0.000 claims 1
NAXONVFZNDSIOA-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-methyl-n-(5-methylpyridin-2-yl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(N)=O)C=C1 NAXONVFZNDSIOA-UHFFFAOYSA-N 0.000 claims 1
JISQQVJTJDFXRB-UHFFFAOYSA-N 3-(4-chloro-2-methylphenyl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)C=C1C JISQQVJTJDFXRB-UHFFFAOYSA-N 0.000 claims 1
SGBLYEXNDXRPMA-UHFFFAOYSA-N 3-(4-chloro-3-cyanophenyl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)C(C#N)=C1 SGBLYEXNDXRPMA-UHFFFAOYSA-N 0.000 claims 1
OITHLARCOTZUEK-UHFFFAOYSA-N 3-(4-chloro-3-fluorophenyl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)C(F)=C1 OITHLARCOTZUEK-UHFFFAOYSA-N 0.000 claims 1
UMAKYAPGHSOVND-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(2,4-dichlorophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)C=C1 UMAKYAPGHSOVND-UHFFFAOYSA-N 0.000 claims 1
STYUAVUVDLMNKN-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(3,4-difluorophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C(F)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)C=C1 STYUAVUVDLMNKN-UHFFFAOYSA-N 0.000 claims 1
AQUJRJPVKDBLDU-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)C=C1 AQUJRJPVKDBLDU-UHFFFAOYSA-N 0.000 claims 1
BZTQLIDILRQIMU-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(4-fluorophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)C=C1 BZTQLIDILRQIMU-UHFFFAOYSA-N 0.000 claims 1
JZTIMGRWTFVWFJ-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-methyl-n-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)C=C1 JZTIMGRWTFVWFJ-UHFFFAOYSA-N 0.000 claims 1
QABLIIFVAKVEQP-UHFFFAOYSA-N 3-(4-cyanophenyl)-n-methyl-n-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C#N)C=C1 QABLIIFVAKVEQP-UHFFFAOYSA-N 0.000 claims 1
MDUHSHBLKFIPKF-UHFFFAOYSA-N 3-(4-cyanophenyl)-n-methyl-n-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C#N)C=C1 MDUHSHBLKFIPKF-UHFFFAOYSA-N 0.000 claims 1
XMGOWFQZRLEQKO-UHFFFAOYSA-N 3-(4-methoxy-2-methylphenyl)-n-[6-(4-methoxy-2-methylphenyl)pyridin-3-yl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CC1=CC(OC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=NC(=CC=1)C=1C(=CC(OC)=CC=1)C)N=C2 XMGOWFQZRLEQKO-UHFFFAOYSA-N 0.000 claims 1
RGRQSJUQYXOSQE-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(C)(C)C)C=C1 RGRQSJUQYXOSQE-UHFFFAOYSA-N 0.000 claims 1
KVMMUMGPMZYKDZ-UHFFFAOYSA-N 3-(5-chloropyridin-2-yl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)C=N1 KVMMUMGPMZYKDZ-UHFFFAOYSA-N 0.000 claims 1
MEBDGPOPMCFLJW-UHFFFAOYSA-N 3-(6-acetamidopyridin-3-yl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(NC(C)=O)N=C1 MEBDGPOPMCFLJW-UHFFFAOYSA-N 0.000 claims 1
LZSXEDCSWZBBFS-UHFFFAOYSA-N 3-(6-acetamidopyridin-3-yl)-n-methyl-n-(5-methylpyridin-2-yl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(NC(C)=O)N=C1 LZSXEDCSWZBBFS-UHFFFAOYSA-N 0.000 claims 1
PZCLXCDSDSRXKD-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(N)N=C1 PZCLXCDSDSRXKD-UHFFFAOYSA-N 0.000 claims 1
GELPLCWUNHFMSU-UHFFFAOYSA-N 3-(6-chloropyridin-3-yl)-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)N=C1 GELPLCWUNHFMSU-UHFFFAOYSA-N 0.000 claims 1
WOYMWMNNHBJCRW-UHFFFAOYSA-N 3-[2-chloro-4-(trifluoromethyl)phenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1Cl WOYMWMNNHBJCRW-UHFFFAOYSA-N 0.000 claims 1
RQFCTILRHZUTAM-UHFFFAOYSA-N 3-[4-(1-amino-2-methyl-1-oxopropan-2-yl)oxyphenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(OC(C)(C)C(N)=O)C=C1 RQFCTILRHZUTAM-UHFFFAOYSA-N 0.000 claims 1
ZDYLBVVQUQKLRN-UHFFFAOYSA-N 3-[4-(1-amino-2-methylpropan-2-yl)oxyphenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(OC(C)(C)CN)C=C1 ZDYLBVVQUQKLRN-UHFFFAOYSA-N 0.000 claims 1
IQXPGWYFWBBKMK-UHFFFAOYSA-N 3-[4-(2-aminoethoxy)phenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(OCCN)C=C1 IQXPGWYFWBBKMK-UHFFFAOYSA-N 0.000 claims 1
OFPMKWATRNGGDR-UHFFFAOYSA-N 3-[4-(2-aminoethoxy)phenyl]-n-methyl-n-(5-methylpyridin-2-yl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(OCCN)C=C1 OFPMKWATRNGGDR-UHFFFAOYSA-N 0.000 claims 1
KHDKYBZVFJSCMX-UHFFFAOYSA-N 3-[4-(5-amino-1,3,4-thiadiazol-2-yl)phenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=NN=C(N)S1 KHDKYBZVFJSCMX-UHFFFAOYSA-N 0.000 claims 1
JRBSOPHFFWJVBC-UHFFFAOYSA-N 3-[4-(aminomethyl)phenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(CN)C=C1 JRBSOPHFFWJVBC-UHFFFAOYSA-N 0.000 claims 1
PEKHZNSZRYISTL-UHFFFAOYSA-N 3-[4-(cyanomethoxy)phenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(OCC#N)C=C1 PEKHZNSZRYISTL-UHFFFAOYSA-N 0.000 claims 1
QOZVJIYICNLTFB-UHFFFAOYSA-N 3-[4-(difluoromethoxy)phenyl]-n-(3,4-difluorophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C(F)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(OC(F)F)C=C1 QOZVJIYICNLTFB-UHFFFAOYSA-N 0.000 claims 1
NUKYDHSBSGEQMA-UHFFFAOYSA-N 3-[4-(difluoromethoxy)phenyl]-n-(4-fluorophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(OC(F)F)C=C1 NUKYDHSBSGEQMA-UHFFFAOYSA-N 0.000 claims 1
ZXXRPVCLYNSTCZ-UHFFFAOYSA-N 3-[4-(difluoromethoxy)phenyl]-n-methyl-n-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(OC(F)F)C=C1 ZXXRPVCLYNSTCZ-UHFFFAOYSA-N 0.000 claims 1
MMZMTZXGAPGEFA-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-n-(4-fluorophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(F)=CC=1)N=C2 MMZMTZXGAPGEFA-UHFFFAOYSA-N 0.000 claims 1
QZSRVYZKFXWKBE-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-n-methyl-n-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)S(C)(=O)=O)N=C2 QZSRVYZKFXWKBE-UHFFFAOYSA-N 0.000 claims 1
OYZZZRLNVONJFM-UHFFFAOYSA-N 3-[4-[(2-amino-2-cyclobutylacetyl)amino]phenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1NC(=O)C(N)C1CCC1 OYZZZRLNVONJFM-UHFFFAOYSA-N 0.000 claims 1
ARYGTZIFJUPHOE-UHFFFAOYSA-N 3-[4-[(2-amino-2-methylpropanoyl)amino]phenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(NC(=O)C(C)(C)N)C=C1 ARYGTZIFJUPHOE-UHFFFAOYSA-N 0.000 claims 1
JVUPTGUTGYRUQR-UHFFFAOYSA-N 3-[4-[(2-amino-2-methylpropyl)amino]phenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(NCC(C)(C)N)C=C1 JVUPTGUTGYRUQR-UHFFFAOYSA-N 0.000 claims 1
PQWDRCIADMCILA-UHFFFAOYSA-N 3-[4-[(2-aminoacetyl)amino]phenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(NC(=O)CN)C=C1 PQWDRCIADMCILA-UHFFFAOYSA-N 0.000 claims 1
IQYLGFHTTIEJLO-OAHLLOKOSA-N 3-[4-[[(2r)-2-aminopropanoyl]amino]phenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(NC(=O)[C@H](N)C)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 IQYLGFHTTIEJLO-OAHLLOKOSA-N 0.000 claims 1
IUVQTRSNGXLCQI-MHZLTWQESA-N 3-[4-[[(2s)-2-amino-2-cyclohexylacetyl]amino]phenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1([C@H](N)C(=O)NC2=CC=C(C=C2)C=2N3C=C(N=CC3=NC=2)C(=O)N(C)C=2C=CC(=CC=2)C#N)CCCCC1 IUVQTRSNGXLCQI-MHZLTWQESA-N 0.000 claims 1
WTJXDUDOGPGXSS-DEOSSOPVSA-N 3-[4-[[(2s)-2-amino-2-cyclopropylacetyl]amino]phenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1([C@H](N)C(=O)NC2=CC=C(C=C2)C=2N3C=C(N=CC3=NC=2)C(=O)N(C)C=2C=CC(=CC=2)C#N)CC1 WTJXDUDOGPGXSS-DEOSSOPVSA-N 0.000 claims 1
IQYLGFHTTIEJLO-HNNXBMFYSA-N 3-[4-[[(2s)-2-aminopropanoyl]amino]phenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(NC(=O)[C@@H](N)C)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 IQYLGFHTTIEJLO-HNNXBMFYSA-N 0.000 claims 1
XWHQPAKOBJYTMX-UHFFFAOYSA-N 3-[4-chloro-2-(trifluoromethyl)phenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)C=C1C(F)(F)F XWHQPAKOBJYTMX-UHFFFAOYSA-N 0.000 claims 1
GUYFAVXLXBGODP-UHFFFAOYSA-N 3-[4-chloro-3-(trifluoromethyl)phenyl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)C(C(F)(F)F)=C1 GUYFAVXLXBGODP-UHFFFAOYSA-N 0.000 claims 1
WJIYOSRDZIKNQJ-UHFFFAOYSA-N 3-[6-(4-acetylpiperazin-1-yl)pyridin-3-yl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=N1)=CC=C1N1CCN(C(C)=O)CC1 WJIYOSRDZIKNQJ-UHFFFAOYSA-N 0.000 claims 1
ZWLSUPMMZIQQKJ-UHFFFAOYSA-N 3-[6-[(2-aminoacetyl)amino]pyridin-3-yl]-n-(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(NC(=O)CN)N=C1 ZWLSUPMMZIQQKJ-UHFFFAOYSA-N 0.000 claims 1
YNWCUCSDUMVJKR-UHFFFAOYSA-N 4-[(7-chloroquinolin-4-yl)amino]-2-(pyrrolidin-1-ylmethyl)phenol Chemical compound OC1=CC=C(NC=2C3=CC=C(Cl)C=C3N=CC=2)C=C1CN1CCCC1 YNWCUCSDUMVJKR-UHFFFAOYSA-N 0.000 claims 1
FNEWLPMGCZVFHT-UHFFFAOYSA-N 4-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carbonyl]-1,3-dihydroquinoxalin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CN=C2N1C=C(C(=O)N1C3=CC=CC=C3NC(=O)C1)N=C2 FNEWLPMGCZVFHT-UHFFFAOYSA-N 0.000 claims 1
PPYXXOARBRIFIX-UHFFFAOYSA-N 4-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carbonyl]-2,3-dihydro-1,4-benzoxazine-7-carbonitrile Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CN=C2N1C=C(C(=O)N1C3=CC=C(C=C3OCC1)C#N)N=C2 PPYXXOARBRIFIX-UHFFFAOYSA-N 0.000 claims 1
JTRNRHGVANAJBM-UHFFFAOYSA-N 4-[6-(6-fluoro-3,4-dihydro-2h-quinoline-1-carbonyl)imidazo[1,2-a]pyrazin-3-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CN=C2N1C=C(C(=O)N1C3=CC=C(F)C=C3CCC1)N=C2 JTRNRHGVANAJBM-UHFFFAOYSA-N 0.000 claims 1
GGUVDIQUNSXJHW-UHFFFAOYSA-N 4-[6-[(4-chloro-n-methylanilino)methyl]imidazo[1,2-a]pyrazin-3-yl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=C2N1C=C(CN(C)C=1C=CC(Cl)=CC=1)N=C2 GGUVDIQUNSXJHW-UHFFFAOYSA-N 0.000 claims 1
NKYBYKPFKRDHCZ-UHFFFAOYSA-N 4-[6-[(4-fluoro-n-methylanilino)methyl]imidazo[1,2-a]pyrazin-3-yl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=C2N1C=C(CN(C)C=1C=CC(F)=CC=1)N=C2 NKYBYKPFKRDHCZ-UHFFFAOYSA-N 0.000 claims 1
NCRMSGFWGNMCCM-UHFFFAOYSA-N 4-[6-[[methyl-(5-methylpyridin-2-yl)amino]methyl]imidazo[1,2-a]pyrazin-3-yl]benzamide Chemical compound C=1C=C(C)C=NC=1N(C)CC(N=CC1=NC=2)=CN1C=2C1=CC=C(C(N)=O)C=C1 NCRMSGFWGNMCCM-UHFFFAOYSA-N 0.000 claims 1
ZMFPZEUVGVOOBC-UHFFFAOYSA-N 4-[[3-(4-chlorophenyl)imidazo[1,2-a]pyrazin-6-yl]methyl-methylamino]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1N(C)CC(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)C=C1 ZMFPZEUVGVOOBC-UHFFFAOYSA-N 0.000 claims 1
JTJZHYLYQVVZTC-UHFFFAOYSA-N 4-[[3-[4-(5-amino-1,3,4-thiadiazol-2-yl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl-methylamino]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1N(C)CC(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=NN=C(N)S1 JTJZHYLYQVVZTC-UHFFFAOYSA-N 0.000 claims 1
UOORRAAVCRSARI-UHFFFAOYSA-N 4-[[3-[4-(difluoromethoxy)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl-methylamino]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1N(C)CC(N=CC1=NC=2)=CN1C=2C1=CC=C(OC(F)F)C=C1 UOORRAAVCRSARI-UHFFFAOYSA-N 0.000 claims 1
HAZZWVSDYMIQSW-UHFFFAOYSA-N 4-[[3-[4-(dimethylamino)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl-methylamino]benzonitrile Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=C2N1C=C(CN(C)C=1C=CC(=CC=1)C#N)N=C2 HAZZWVSDYMIQSW-UHFFFAOYSA-N 0.000 claims 1
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RDDOHSVECIYITM-UHFFFAOYSA-N 4-[methyl-[[3-(1-methylindazol-5-yl)imidazo[1,2-a]pyrazin-6-yl]methyl]amino]benzonitrile Chemical compound C=1N2C(C=3C=C4C=NN(C)C4=CC=3)=CN=C2C=NC=1CN(C)C1=CC=C(C#N)C=C1 RDDOHSVECIYITM-UHFFFAOYSA-N 0.000 claims 1
JRGSKXIEVFDPCI-UHFFFAOYSA-N 4-[methyl-[[3-[4-(1h-pyrazol-5-yl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl]amino]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1N(C)CC(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=CC=NN1 JRGSKXIEVFDPCI-UHFFFAOYSA-N 0.000 claims 1
GOBGWJAGMLOUHN-UHFFFAOYSA-N 4-[methyl-[[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl]amino]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1N(C)CC(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 GOBGWJAGMLOUHN-UHFFFAOYSA-N 0.000 claims 1
LUBUTTBEBGYNJN-UHFFFAOYSA-N 4-amino-n-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamide;5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1.COC1=NC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1OC LUBUTTBEBGYNJN-UHFFFAOYSA-N 0.000 claims 1
UWWNXFLISDYABL-UHFFFAOYSA-N 4-chloro-n-[[3-(4-chlorophenyl)imidazo[1,2-a]pyrazin-6-yl]methyl]-n-methylaniline Chemical compound C=1C=C(Cl)C=CC=1N(C)CC(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)C=C1 UWWNXFLISDYABL-UHFFFAOYSA-N 0.000 claims 1
ICAWQTXSJONHFE-UHFFFAOYSA-N 4-chloro-n-[[3-[4-(difluoromethoxy)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl]-n-methylaniline Chemical compound C=1C=C(Cl)C=CC=1N(C)CC(N=CC1=NC=2)=CN1C=2C1=CC=C(OC(F)F)C=C1 ICAWQTXSJONHFE-UHFFFAOYSA-N 0.000 claims 1
NPZDFFMJMOZBTD-UHFFFAOYSA-N 4-chloro-n-methyl-n-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C=1N2C(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2C=NC=1N(C)C(=O)C1=CC=C(Cl)C=C1 NPZDFFMJMOZBTD-UHFFFAOYSA-N 0.000 claims 1
RZKLTMOIQVTBGV-UHFFFAOYSA-N 4-chloro-n-methyl-n-[[3-(1-methylindazol-5-yl)imidazo[1,2-a]pyrazin-6-yl]methyl]aniline Chemical compound C=1N2C(C=3C=C4C=NN(C)C4=CC=3)=CN=C2C=NC=1CN(C)C1=CC=C(Cl)C=C1 RZKLTMOIQVTBGV-UHFFFAOYSA-N 0.000 claims 1
LRLJGYJYSPUNSN-UHFFFAOYSA-N 4-chloro-n-methyl-n-[[3-[4-(1h-pyrazol-5-yl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl]aniline Chemical compound C=1C=C(Cl)C=CC=1N(C)CC(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=CC=NN1 LRLJGYJYSPUNSN-UHFFFAOYSA-N 0.000 claims 1
AQOVHDSEWPPEJS-UHFFFAOYSA-N 4-cyano-n-methyl-n-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C=1N2C(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2C=NC=1N(C)C(=O)C1=CC=C(C#N)C=C1 AQOVHDSEWPPEJS-UHFFFAOYSA-N 0.000 claims 1
ZGLWEJQGKQXIER-UHFFFAOYSA-N 4-fluoro-n-methyl-n-[3-(1h-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C=1N2C(C=3C=C4C=CNC4=NC=3)=CN=C2C=NC=1N(C)C(=O)C1=CC=C(F)C=C1 ZGLWEJQGKQXIER-UHFFFAOYSA-N 0.000 claims 1
FNAKBXUKRBOSCA-UHFFFAOYSA-N 4-fluoro-n-methyl-n-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C=1N2C(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2C=NC=1N(C)C(=O)C1=CC=C(F)C=C1 FNAKBXUKRBOSCA-UHFFFAOYSA-N 0.000 claims 1
SSZMINSXWJDYTL-UHFFFAOYSA-N 4-fluoro-n-methyl-n-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]piperidine-1-carboxamide Chemical compound C=1N2C(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2C=NC=1N(C)C(=O)N1CCC(F)CC1 SSZMINSXWJDYTL-UHFFFAOYSA-N 0.000 claims 1
RNJUVWUPYBPQGN-UHFFFAOYSA-N 4-fluoro-n-methyl-n-[[3-(1-methylindazol-5-yl)imidazo[1,2-a]pyrazin-6-yl]methyl]aniline Chemical compound C=1N2C(C=3C=C4C=NN(C)C4=CC=3)=CN=C2C=NC=1CN(C)C1=CC=C(F)C=C1 RNJUVWUPYBPQGN-UHFFFAOYSA-N 0.000 claims 1
VIUJUTFWIWQCTN-UHFFFAOYSA-N 4-fluoro-n-methyl-n-[[3-[4-(1h-pyrazol-5-yl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl]aniline Chemical compound C=1C=C(F)C=CC=1N(C)CC(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=CC=NN1 VIUJUTFWIWQCTN-UHFFFAOYSA-N 0.000 claims 1
ROMFEAVKLCINSO-UHFFFAOYSA-N 4-methoxy-n-methyl-n-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)N(C)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 ROMFEAVKLCINSO-UHFFFAOYSA-N 0.000 claims 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
RCWUDVYOLSWOSK-UHFFFAOYSA-N 4-tert-butyl-n-methyl-n-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C=1N2C(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2C=NC=1N(C)C(=O)C1=CC=C(C(C)(C)C)C=C1 RCWUDVYOLSWOSK-UHFFFAOYSA-N 0.000 claims 1
NSQMPVXXZJTHLO-UHFFFAOYSA-N 5-chloro-n-methyl-n-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]pyridine-2-carboxamide Chemical compound C=1N2C(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2C=NC=1N(C)C(=O)C1=CC=C(Cl)C=N1 NSQMPVXXZJTHLO-UHFFFAOYSA-N 0.000 claims 1
XNDYLIDDFXZCLI-UHFFFAOYSA-N 6-chloro-n-methyl-n-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]pyridine-3-carboxamide Chemical compound C=1N2C(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2C=NC=1N(C)C(=O)C1=CC=C(Cl)N=C1 XNDYLIDDFXZCLI-UHFFFAOYSA-N 0.000 claims 1
HMDSIBQZBJTPMR-UHFFFAOYSA-N 6-chloro-n-methyl-n-[[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl]pyridin-3-amine Chemical compound C=1C=C(Cl)N=CC=1N(C)CC(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 HMDSIBQZBJTPMR-UHFFFAOYSA-N 0.000 claims 1
JCGVRWZLOMOORR-UHFFFAOYSA-N 6-fluoro-1-[[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl]-3,4-dihydro-2h-quinoline Chemical compound C1CCC2=CC(F)=CC=C2N1CC(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 JCGVRWZLOMOORR-UHFFFAOYSA-N 0.000 claims 1
DLYPREQTTOHKSM-UHFFFAOYSA-N 7-chloro-n-[[2-[(dimethylamino)methyl]cyclopenta-1,4-dien-1-yl]methyl]quinolin-4-amine;cyclopenta-1,3-diene;iron(2+) Chemical compound [Fe+2].C1C=CC=[C-]1.C1=[C-]CC(CN(C)C)=C1CNC1=CC=NC2=CC(Cl)=CC=C12 DLYPREQTTOHKSM-UHFFFAOYSA-N 0.000 claims 1
AGRSBHPPVUCMBP-UHFFFAOYSA-N 7-fluoro-4-[[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl]-2,3-dihydro-1,4-benzoxazine Chemical compound C1COC2=CC(F)=CC=C2N1CC(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 AGRSBHPPVUCMBP-UHFFFAOYSA-N 0.000 claims 1
OVCDSSHSILBFBN-UHFFFAOYSA-N Amodiaquine Chemical compound C1=C(O)C(CN(CC)CC)=CC(NC=2C3=CC=C(Cl)C=C3N=CC=2)=C1 OVCDSSHSILBFBN-UHFFFAOYSA-N 0.000 claims 1
125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
BRJULSXZDFYSPG-MSMJXPJBSA-N CC(C)(N)NC(=O)C[C@H]1CC[C@]2(CC1)OOC1(O2)[C@H]2CC3CC(C2)C[C@H]1C3 Chemical compound CC(C)(N)NC(=O)C[C@H]1CC[C@]2(CC1)OOC1(O2)[C@H]2CC3CC(C2)C[C@H]1C3 BRJULSXZDFYSPG-MSMJXPJBSA-N 0.000 claims 1
235000001258 Cinchona calisaya Nutrition 0.000 claims 1
QINMGNWRAYORQA-UHFFFAOYSA-N N-(6-chloropyridin-3-yl)-3-(1H-indol-2-yl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CN(C(=O)c1cn2c(cnc2cn1)-c1cc2ccccc2[nH]1)c1ccc(Cl)nc1 QINMGNWRAYORQA-UHFFFAOYSA-N 0.000 claims 1
BYFKSCOTQGJKTJ-UHFFFAOYSA-N [3-(1-ethylpyrazol-4-yl)imidazo[1,2-a]pyrazin-6-yl]-(6-fluoro-3,4-dihydro-2h-quinolin-1-yl)methanone Chemical compound C1=NN(CC)C=C1C1=CN=C2N1C=C(C(=O)N1C3=CC=C(F)C=C3CCC1)N=C2 BYFKSCOTQGJKTJ-UHFFFAOYSA-N 0.000 claims 1
QHUSVZZEBIOELW-UHFFFAOYSA-N [3-(2,3-dihydro-1-benzofuran-5-yl)imidazo[1,2-a]pyrazin-6-yl]-(6-fluoro-3,4-dihydro-2h-quinolin-1-yl)methanone Chemical compound C1=C2OCCC2=CC(C=2N3C=C(N=CC3=NC=2)C(=O)N2C3=CC=C(C=C3CCC2)F)=C1 QHUSVZZEBIOELW-UHFFFAOYSA-N 0.000 claims 1
KAFGFTYFGACOET-UHFFFAOYSA-N [3-[3-(dimethylamino)phenyl]imidazo[1,2-a]pyrazin-6-yl]-(6-fluoro-3,4-dihydro-2h-quinolin-1-yl)methanone Chemical compound CN(C)C1=CC=CC(C=2N3C=C(N=CC3=NC=2)C(=O)N2C3=CC=C(F)C=C3CCC2)=C1 KAFGFTYFGACOET-UHFFFAOYSA-N 0.000 claims 1
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
229960001444 amodiaquine Drugs 0.000 claims 1
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229960004191 artemisinin Drugs 0.000 claims 1
BLUAFEHZUWYNDE-NNWCWBAJSA-N artemisinin Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-NNWCWBAJSA-N 0.000 claims 1
229930101531 artemisinin Natural products 0.000 claims 1
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BJDCWCLMFKKGEE-ISOSDAIHSA-N artenimol Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@H](O)[C@@H]4C BJDCWCLMFKKGEE-ISOSDAIHSA-N 0.000 claims 1
229950007854 arterolane Drugs 0.000 claims 1
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FIHJKUPKCHIPAT-AHIGJZGOSA-N artesunate Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@@H](OC(=O)CCC(O)=O)[C@@H]4C FIHJKUPKCHIPAT-AHIGJZGOSA-N 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
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KUCQYCKVKVOKAY-CTYIDZIISA-N atovaquone Chemical compound C1([C@H]2CC[C@@H](CC2)C2=C(C(C3=CC=CC=C3C2=O)=O)O)=CC=C(Cl)C=C1 KUCQYCKVKVOKAY-CTYIDZIISA-N 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
229960003677 chloroquine Drugs 0.000 claims 1
WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 claims 1
ISZNZKHCRKXXAU-UHFFFAOYSA-N chlorproguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C(Cl)=C1 ISZNZKHCRKXXAU-UHFFFAOYSA-N 0.000 claims 1
229950000764 chlorproguanil Drugs 0.000 claims 1
125000004802 cyanophenyl group Chemical group 0.000 claims 1
229930016266 dihydroartemisinin Natural products 0.000 claims 1
SXYIRMFQILZOAM-HVNFFKDJSA-N dihydroartemisinin methyl ether Chemical compound C1C[C@H]2[C@H](C)CC[C@H]3[C@@H](C)[C@@H](OC)O[C@H]4[C@]32OO[C@@]1(C)O4 SXYIRMFQILZOAM-HVNFFKDJSA-N 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
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MBVAHHOKMIRXLP-UHFFFAOYSA-N imidazo[1,2-a]pyrazine Chemical compound C1=CN=CC2=NC=CN21 MBVAHHOKMIRXLP-UHFFFAOYSA-N 0.000 claims 1
FXBLRUPBVBHCTR-UHFFFAOYSA-N imidazo[1,2-a]pyrazine-3-carboxylic acid Chemical compound C1=NC=CN2C(C(=O)O)=CN=C21 FXBLRUPBVBHCTR-UHFFFAOYSA-N 0.000 claims 1
HWNHQKGIFMHZHG-UHFFFAOYSA-N imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound NC(=O)c1cn2ccnc2cn1 HWNHQKGIFMHZHG-UHFFFAOYSA-N 0.000 claims 1
229960001962 mefloquine Drugs 0.000 claims 1
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125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
MTWWDMRDGKZSIE-UHFFFAOYSA-N methyl n-[4-[6-[[methyl-(5-methylpyridin-2-yl)amino]methyl]imidazo[1,2-a]pyrazin-3-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C1=CN=C2N1C=C(CN(C)C=1N=CC(C)=CC=1)N=C2 MTWWDMRDGKZSIE-UHFFFAOYSA-N 0.000 claims 1
AUZAWJZEFTTYHU-UHFFFAOYSA-N methyl n-[5-[6-[methyl-(5-methylpyridin-2-yl)carbamoyl]imidazo[1,2-a]pyrazin-3-yl]pyridin-2-yl]carbamate Chemical compound C1=NC(NC(=O)OC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1N=CC(C)=CC=1)N=C2 AUZAWJZEFTTYHU-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 claims 1
YMCDPQGGEFLOQC-UHFFFAOYSA-N morpholin-4-yl-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CN=C2N1C=C(C(=O)N1CCOCC1)N=C2 YMCDPQGGEFLOQC-UHFFFAOYSA-N 0.000 claims 1
RVFOGKBQZUFNDT-UHFFFAOYSA-N n,3-bis(4-chlorophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)C=C1 RVFOGKBQZUFNDT-UHFFFAOYSA-N 0.000 claims 1
JHCFUKAYCXWMPM-UHFFFAOYSA-N n,3-bis(4-cyanophenyl)-n-methyl-2-(trifluoromethyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2C(F)(F)F)=CN1C=2C1=CC=C(C#N)C=C1 JHCFUKAYCXWMPM-UHFFFAOYSA-N 0.000 claims 1
AEVJOAXSUIBWAI-UHFFFAOYSA-N n,3-bis(4-cyanophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C#N)C=C1 AEVJOAXSUIBWAI-UHFFFAOYSA-N 0.000 claims 1
SKKUOQAXXVWJHF-UHFFFAOYSA-N n,3-bis[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 SKKUOQAXXVWJHF-UHFFFAOYSA-N 0.000 claims 1
UCLMEFVGBIQPGS-UHFFFAOYSA-N n,4-dimethyl-n-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C=1N2C(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2C=NC=1N(C)C(=O)C1=CC=C(C)C=C1 UCLMEFVGBIQPGS-UHFFFAOYSA-N 0.000 claims 1
HHWNBCHZKZBRKY-UHFFFAOYSA-N n,4-dimethyl-n-[[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl]aniline Chemical compound C=1C=C(C)C=CC=1N(C)CC(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 HHWNBCHZKZBRKY-UHFFFAOYSA-N 0.000 claims 1
UFYSSXQSKBUYFD-UHFFFAOYSA-N n,5-dimethyl-n-[[3-(1-methylindazol-5-yl)imidazo[1,2-a]pyrazin-6-yl]methyl]pyridin-2-amine Chemical compound C=1N2C(C=3C=C4C=NN(C)C4=CC=3)=CN=C2C=NC=1CN(C)C1=CC=C(C)C=N1 UFYSSXQSKBUYFD-UHFFFAOYSA-N 0.000 claims 1
LRJZQYSTXGPFFR-UHFFFAOYSA-N n,5-dimethyl-n-[[3-[4-(1h-pyrazol-5-yl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl]pyridin-2-amine Chemical compound C=1C=C(C)C=NC=1N(C)CC(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=CC=NN1 LRJZQYSTXGPFFR-UHFFFAOYSA-N 0.000 claims 1
FNMXWHKPUAONHT-UHFFFAOYSA-N n,5-dimethyl-n-[[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl]pyridin-2-amine Chemical compound C=1C=C(C)C=NC=1N(C)CC(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 FNMXWHKPUAONHT-UHFFFAOYSA-N 0.000 claims 1
NNBRDZIPILCAAD-UHFFFAOYSA-N n,5-dimethyl-n-[[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl]pyridin-3-amine Chemical compound C=1N=CC(C)=CC=1N(C)CC(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 NNBRDZIPILCAAD-UHFFFAOYSA-N 0.000 claims 1
UIMHSRIOAYFKTR-UHFFFAOYSA-N n-(1,3-benzothiazol-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound N=1C2=CC=CC=C2SC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 UIMHSRIOAYFKTR-UHFFFAOYSA-N 0.000 claims 1
KUQTVGFRHMUANQ-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-3-(4-methoxyphenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C(=CC(Cl)=CC=1)Cl)N=C2 KUQTVGFRHMUANQ-UHFFFAOYSA-N 0.000 claims 1
WAZLHFHINFSMQX-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-n-methyl-3-(4-methylphenyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C)C=C1 WAZLHFHINFSMQX-UHFFFAOYSA-N 0.000 claims 1
XLHOOGCDJRFBAL-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 XLHOOGCDJRFBAL-UHFFFAOYSA-N 0.000 claims 1
HPTGJTWYFFLXKV-UHFFFAOYSA-N n-(2,4-difluorophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C=C(F)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 HPTGJTWYFFLXKV-UHFFFAOYSA-N 0.000 claims 1
GXGSVHXOEKTVIZ-UHFFFAOYSA-N n-(2,6-dichloropyridin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)N=C(Cl)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 GXGSVHXOEKTVIZ-UHFFFAOYSA-N 0.000 claims 1
ILYBFJMCBHNDPX-UHFFFAOYSA-N n-(2-aminoethyl)-n-(4-cyanophenyl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(CCN)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 ILYBFJMCBHNDPX-UHFFFAOYSA-N 0.000 claims 1
IYEXXXHYFDJNGP-UHFFFAOYSA-N n-(2-chloro-1,3-thiazol-5-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N=C(Cl)SC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 IYEXXXHYFDJNGP-UHFFFAOYSA-N 0.000 claims 1
YRKXBSCHCQGCAP-UHFFFAOYSA-N n-(2-chloro-5-methylpyridin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C(C)=CN=C(Cl)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 YRKXBSCHCQGCAP-UHFFFAOYSA-N 0.000 claims 1
MERLEQUEZBDLDN-UHFFFAOYSA-N n-(2-chlorophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=CC=C(Cl)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 MERLEQUEZBDLDN-UHFFFAOYSA-N 0.000 claims 1
OTPNCCPNJPWITE-UHFFFAOYSA-N n-(2-fluorophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=CC=C(F)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 OTPNCCPNJPWITE-UHFFFAOYSA-N 0.000 claims 1
KZLNGUMTNSYUSK-UHFFFAOYSA-N n-(2-fluoropyridin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=CN=C(F)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 KZLNGUMTNSYUSK-UHFFFAOYSA-N 0.000 claims 1
YLZHKGDOGMGXSN-UHFFFAOYSA-N n-(2-methoxyphenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound COC1=CC=CC=C1N(C)C(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 YLZHKGDOGMGXSN-UHFFFAOYSA-N 0.000 claims 1
DTAPCXVVDFLATN-UHFFFAOYSA-N n-(2-methoxypyridin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound COC1=NC=CC=C1N(C)C(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 DTAPCXVVDFLATN-UHFFFAOYSA-N 0.000 claims 1
UDZXHWRFPCZFBY-UHFFFAOYSA-N n-(2-methoxypyridin-4-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=NC(OC)=CC(N(C)C(=O)C=2N=CC3=NC=C(N3C=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 UDZXHWRFPCZFBY-UHFFFAOYSA-N 0.000 claims 1
LTCWEAKADOYTEX-UHFFFAOYSA-N n-(2-methoxypyrimidin-5-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=NC(OC)=NC=C1N(C)C(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 LTCWEAKADOYTEX-UHFFFAOYSA-N 0.000 claims 1
BKACWZYIVBZIAU-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 BKACWZYIVBZIAU-UHFFFAOYSA-N 0.000 claims 1
WGNCTTMBWWHUEX-UHFFFAOYSA-N n-(3,4-difluorophenyl)-3-(4-methoxyphenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=C(F)C(F)=CC=1)N=C2 WGNCTTMBWWHUEX-UHFFFAOYSA-N 0.000 claims 1
JGVPCFKCBQIWQQ-UHFFFAOYSA-N n-(3,4-difluorophenyl)-3-[4-(dimethylamino)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=C(F)C(F)=CC=1)N=C2 JGVPCFKCBQIWQQ-UHFFFAOYSA-N 0.000 claims 1
PPHPAHZCIYLQKW-UHFFFAOYSA-N n-(3,4-difluorophenyl)-n-methyl-3-(4-methylphenyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C(F)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C)C=C1 PPHPAHZCIYLQKW-UHFFFAOYSA-N 0.000 claims 1
QCOANIUKASEJLZ-UHFFFAOYSA-N n-(3,4-difluorophenyl)-n-methyl-3-[4-(1h-pyrazol-5-yl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C(F)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=CC=NN1 QCOANIUKASEJLZ-UHFFFAOYSA-N 0.000 claims 1
UBDKFDAHEVRRQI-UHFFFAOYSA-N n-(3,4-difluorophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C(F)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 UBDKFDAHEVRRQI-UHFFFAOYSA-N 0.000 claims 1
WFGWSRKEHYKCSJ-UHFFFAOYSA-N n-(3-bromo-4-fluorophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C(Br)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 WFGWSRKEHYKCSJ-UHFFFAOYSA-N 0.000 claims 1
BKWVBWRGSVCMAF-UHFFFAOYSA-N n-(3-bromophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=CC(Br)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 BKWVBWRGSVCMAF-UHFFFAOYSA-N 0.000 claims 1
NYRXFRXJCRTJDO-UHFFFAOYSA-N n-(3-chloro-4-cyanophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C(Cl)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 NYRXFRXJCRTJDO-UHFFFAOYSA-N 0.000 claims 1
VHYQEDQHHCMMNA-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C(Cl)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 VHYQEDQHHCMMNA-UHFFFAOYSA-N 0.000 claims 1
VTTGRUURXOWTDL-UHFFFAOYSA-N n-(3-chlorophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=CC(Cl)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 VTTGRUURXOWTDL-UHFFFAOYSA-N 0.000 claims 1
BJNUJEOUURRZEQ-UHFFFAOYSA-N n-(3-fluorophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=CC(F)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 BJNUJEOUURRZEQ-UHFFFAOYSA-N 0.000 claims 1
MYWBQPOXOOAXPM-UHFFFAOYSA-N n-(3-fluoropyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound N=1C=CC=C(F)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 MYWBQPOXOOAXPM-UHFFFAOYSA-N 0.000 claims 1
UGSYICDTDBRDPR-UHFFFAOYSA-N n-(3-methoxyphenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound COC1=CC=CC(N(C)C(=O)C=2N=CC3=NC=C(N3C=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 UGSYICDTDBRDPR-UHFFFAOYSA-N 0.000 claims 1
LHQSRMKWLUXFEQ-UHFFFAOYSA-N n-(3-methoxypyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound COC1=CC=CN=C1N(C)C(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 LHQSRMKWLUXFEQ-UHFFFAOYSA-N 0.000 claims 1
XBFKSOPIVSMLAY-UHFFFAOYSA-N n-(4-acetylphenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C(C)=O)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 XBFKSOPIVSMLAY-UHFFFAOYSA-N 0.000 claims 1
JCTPJPDHFYHNAR-UHFFFAOYSA-N n-(4-bromophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Br)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 JCTPJPDHFYHNAR-UHFFFAOYSA-N 0.000 claims 1
KLZKSZBJVVSBHT-UHFFFAOYSA-N n-(4-chloro-2-methoxyphenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound COC1=CC(Cl)=CC=C1N(C)C(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 KLZKSZBJVVSBHT-UHFFFAOYSA-N 0.000 claims 1
DEJOWHVGUSMQMT-UHFFFAOYSA-N n-(4-chloro-3-methylphenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)C(C)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 DEJOWHVGUSMQMT-UHFFFAOYSA-N 0.000 claims 1
ZIBXRWAZMKCOED-UHFFFAOYSA-N n-(4-chlorophenyl)-3-(4-methoxyphenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(Cl)=CC=1)N=C2 ZIBXRWAZMKCOED-UHFFFAOYSA-N 0.000 claims 1
RZGPMWFAXPWZCH-UHFFFAOYSA-N n-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(OC(F)F)C=C1 RZGPMWFAXPWZCH-UHFFFAOYSA-N 0.000 claims 1
SPCYZRUWZJPYAT-UHFFFAOYSA-N n-(4-chlorophenyl)-3-[4-(dimethylamino)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(Cl)=CC=1)N=C2 SPCYZRUWZJPYAT-UHFFFAOYSA-N 0.000 claims 1
UALGSQGYUKCAEI-UHFFFAOYSA-N n-(4-chlorophenyl)-n-methyl-3-(4-methylphenyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C)C=C1 UALGSQGYUKCAEI-UHFFFAOYSA-N 0.000 claims 1
CUMYBHNETYGUGV-UHFFFAOYSA-N n-(4-chlorophenyl)-n-methyl-3-[4-(1,3,4-thiadiazol-2-yl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=NN=CS1 CUMYBHNETYGUGV-UHFFFAOYSA-N 0.000 claims 1
SNQJTYNERPNLGA-UHFFFAOYSA-N n-(4-chlorophenyl)-n-methyl-3-[4-(1h-pyrazol-5-yl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=CC=NN1 SNQJTYNERPNLGA-UHFFFAOYSA-N 0.000 claims 1
TYMFFISSODJRDV-UHFFFAOYSA-N n-(4-chlorophenyl)-n-methyl-3-[4-(methylcarbamoyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(Cl)=CC=1)N=C2 TYMFFISSODJRDV-UHFFFAOYSA-N 0.000 claims 1
OUAAGHMHOKEHHF-UHFFFAOYSA-N n-(4-chlorophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 OUAAGHMHOKEHHF-UHFFFAOYSA-N 0.000 claims 1
GHMASZDLRVWDNA-UHFFFAOYSA-N n-(4-cyano-2-fluorophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=C(F)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 GHMASZDLRVWDNA-UHFFFAOYSA-N 0.000 claims 1
BNTNNEYJJRWNFI-UHFFFAOYSA-N n-(4-cyano-2-methoxyphenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound COC1=CC(C#N)=CC=C1N(C)C(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 BNTNNEYJJRWNFI-UHFFFAOYSA-N 0.000 claims 1
KRVRCSWJQROGKQ-UHFFFAOYSA-N n-(4-cyano-3-fluorophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C(F)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 KRVRCSWJQROGKQ-UHFFFAOYSA-N 0.000 claims 1
NYPUHZQNDGOMGK-UHFFFAOYSA-N n-(4-cyanophenyl)-2-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CC=1N=C2C=NC(C(=O)NC=3C=CC(=CC=3)C#N)=CN2C=1C1=CC=C(C(F)(F)F)C=C1 NYPUHZQNDGOMGK-UHFFFAOYSA-N 0.000 claims 1
SQCZRLHRENUKGK-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(1h-indazol-5-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=3C=C4C=NNC4=CC=3)=CN=C2C=NC=1C(=O)N(C)C1=CC=C(C#N)C=C1 SQCZRLHRENUKGK-UHFFFAOYSA-N 0.000 claims 1
RCFSEOLIICBASO-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(1h-indazol-6-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=3C=C4NN=CC4=CC=3)=CN=C2C=NC=1C(=O)N(C)C1=CC=C(C#N)C=C1 RCFSEOLIICBASO-UHFFFAOYSA-N 0.000 claims 1
AJCWZIZQIGXOSJ-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(1h-indol-5-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=3C=C4C=CNC4=CC=3)=CN=C2C=NC=1C(=O)N(C)C1=CC=C(C#N)C=C1 AJCWZIZQIGXOSJ-UHFFFAOYSA-N 0.000 claims 1
MAIHWRVTDYTAEE-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(2,4-dichlorophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)C=C1Cl MAIHWRVTDYTAEE-UHFFFAOYSA-N 0.000 claims 1
CMNXUNNQOGWNRR-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(2-fluoro-4-methoxyphenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound FC1=CC(OC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 CMNXUNNQOGWNRR-UHFFFAOYSA-N 0.000 claims 1
NGQJKLYWYARFIT-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(2-methoxypyrimidin-5-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=NC(OC)=NC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 NGQJKLYWYARFIT-UHFFFAOYSA-N 0.000 claims 1
SCXRDTNHYROHID-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(3,5-difluoropyridin-2-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=NC=C(F)C=C1F SCXRDTNHYROHID-UHFFFAOYSA-N 0.000 claims 1
IEWSURVYQGMDED-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(3-methoxyphenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound COC1=CC=CC(C=2N3C=C(N=CC3=NC=2)C(=O)N(C)C=2C=CC(=CC=2)C#N)=C1 IEWSURVYQGMDED-UHFFFAOYSA-N 0.000 claims 1
NNAPTKCSDUKBMT-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(4-fluorophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(F)C=C1 NNAPTKCSDUKBMT-UHFFFAOYSA-N 0.000 claims 1
LNKGYMXYDNBLOB-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(4-methoxy-2-methylphenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CC1=CC(OC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 LNKGYMXYDNBLOB-UHFFFAOYSA-N 0.000 claims 1
LUIOBNZMXZZEOP-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(4-methoxy-3-methylphenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=C(C)C(OC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 LUIOBNZMXZZEOP-UHFFFAOYSA-N 0.000 claims 1
NUVQMRDZIKBLBJ-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(4-methoxyphenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 NUVQMRDZIKBLBJ-UHFFFAOYSA-N 0.000 claims 1
AFFJDICYNIXAGZ-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(6-cyanopyridin-3-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C#N)N=C1 AFFJDICYNIXAGZ-UHFFFAOYSA-N 0.000 claims 1
SUKVTOAFPDQFEH-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(6-fluoropyridin-2-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=CC(F)=N1 SUKVTOAFPDQFEH-UHFFFAOYSA-N 0.000 claims 1
DFWWRVMDDKLGCF-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(6-methoxypyrazin-2-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound COC1=CN=CC(C=2N3C=C(N=CC3=NC=2)C(=O)N(C)C=2C=CC(=CC=2)C#N)=N1 DFWWRVMDDKLGCF-UHFFFAOYSA-N 0.000 claims 1
VQVZJPRPIJLXJZ-UHFFFAOYSA-N n-(4-cyanophenyl)-3-(6-methoxypyridin-3-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=NC(OC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 VQVZJPRPIJLXJZ-UHFFFAOYSA-N 0.000 claims 1
LOYDSZMBIRBGFH-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[2-(dimethylamino)pyrimidin-5-yl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=NC(N(C)C)=NC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 LOYDSZMBIRBGFH-UHFFFAOYSA-N 0.000 claims 1
KHKVEDFRDMQDBX-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[2-fluoro-4-(trifluoromethyl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1F KHKVEDFRDMQDBX-UHFFFAOYSA-N 0.000 claims 1
RVFHUVCPEVSPHP-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[3-(dimethylamino)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CN(C)C1=CC=CC(C=2N3C=C(N=CC3=NC=2)C(=O)N(C)C=2C=CC(=CC=2)C#N)=C1 RVFHUVCPEVSPHP-UHFFFAOYSA-N 0.000 claims 1
DCSOTVJWANJQSW-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[3-fluoro-4-(trifluoromethyl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C(F)=C1 DCSOTVJWANJQSW-UHFFFAOYSA-N 0.000 claims 1
XCBOBSKUSFUERT-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-(1,1-difluoroethyl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(C)(F)F)C=C1 XCBOBSKUSFUERT-UHFFFAOYSA-N 0.000 claims 1
FLCZWXBGNCONDZ-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-(1-methoxyethyl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(C(C)OC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 FLCZWXBGNCONDZ-UHFFFAOYSA-N 0.000 claims 1
IIUPMPRAEUEPOZ-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-(2,5-dioxoimidazolidin-4-yl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1NC(=O)NC1=O IIUPMPRAEUEPOZ-UHFFFAOYSA-N 0.000 claims 1
LPJOQDICNSPOII-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-(3,5-dimethylpyrazol-1-yl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1N1N=C(C)C=C1C LPJOQDICNSPOII-UHFFFAOYSA-N 0.000 claims 1
JOWHDLFXMOEPQQ-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-(cyclopropylcarbamoyl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C(=O)NC1CC1 JOWHDLFXMOEPQQ-UHFFFAOYSA-N 0.000 claims 1
CVXGALYGHZRIDA-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-(diethylcarbamoyl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 CVXGALYGHZRIDA-UHFFFAOYSA-N 0.000 claims 1
ZFLPNYJRIWXLKO-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-(difluoromethoxy)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(OC(F)F)C=C1 ZFLPNYJRIWXLKO-UHFFFAOYSA-N 0.000 claims 1
IHIJXLUJZFGCFM-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-(difluoromethyl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)F)C=C1 IHIJXLUJZFGCFM-UHFFFAOYSA-N 0.000 claims 1
FQNMAHDDEYLWJH-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-(dimethylamino)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 FQNMAHDDEYLWJH-UHFFFAOYSA-N 0.000 claims 1
KSAQFNUANWQCJF-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-(dimethylcarbamoyl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 KSAQFNUANWQCJF-UHFFFAOYSA-N 0.000 claims 1
NHEVMRGYCNUSBM-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-(dimethylsulfamoyl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 NHEVMRGYCNUSBM-UHFFFAOYSA-N 0.000 claims 1
BAYNMSVTKWJECI-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-(furan-2-yl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=CC=CO1 BAYNMSVTKWJECI-UHFFFAOYSA-N 0.000 claims 1
PRPUBGRCBWBCMJ-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-(methanesulfonamido)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(NS(C)(=O)=O)C=C1 PRPUBGRCBWBCMJ-UHFFFAOYSA-N 0.000 claims 1
XRRHSFKRQOIEIV-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-[(dimethylamino)methyl]phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(CN(C)C)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 XRRHSFKRQOIEIV-UHFFFAOYSA-N 0.000 claims 1
BERDAXBVKFCMKL-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-[2-(dimethylamino)ethoxy]phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(OCCN(C)C)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 BERDAXBVKFCMKL-UHFFFAOYSA-N 0.000 claims 1
AKTGLGXKTPYFPP-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-[2-(dimethylamino)ethylcarbamoyl]phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 AKTGLGXKTPYFPP-UHFFFAOYSA-N 0.000 claims 1
LSYXSIHEVZTRIY-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[4-[methoxy(methyl)carbamoyl]phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(C(=O)N(C)OC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 LSYXSIHEVZTRIY-UHFFFAOYSA-N 0.000 claims 1
GKMMAQLDCDDNHE-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[6-(methanesulfonamido)pyridin-3-yl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(NS(C)(=O)=O)N=C1 GKMMAQLDCDDNHE-UHFFFAOYSA-N 0.000 claims 1
MCEISBGQUKQOHN-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[6-[3-(dimethylamino)propoxy]pyridin-3-yl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=NC(OCCCN(C)C)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 MCEISBGQUKQOHN-UHFFFAOYSA-N 0.000 claims 1
NRFKWBVMBYRCJB-UHFFFAOYSA-N n-(4-cyanophenyl)-3-isoquinolin-6-yl-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=3C=C4C=CN=CC4=CC=3)=CN=C2C=NC=1C(=O)N(C)C1=CC=C(C#N)C=C1 NRFKWBVMBYRCJB-UHFFFAOYSA-N 0.000 claims 1
YNZRVTVSQHVEKK-UHFFFAOYSA-N n-(4-cyanophenyl)-n,2-dimethyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2C)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 YNZRVTVSQHVEKK-UHFFFAOYSA-N 0.000 claims 1
PDKVKTAGLXRVNS-UHFFFAOYSA-N n-(4-cyanophenyl)-n-(2-methoxyethyl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(CCOC)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 PDKVKTAGLXRVNS-UHFFFAOYSA-N 0.000 claims 1
LGJVGFRDNDRZCG-UHFFFAOYSA-N n-(4-cyanophenyl)-n-[2-(dimethylamino)ethyl]-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(CCN(C)C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 LGJVGFRDNDRZCG-UHFFFAOYSA-N 0.000 claims 1
FYDNIKYCQAMAHS-UHFFFAOYSA-N n-(4-cyanophenyl)-n-ethyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(CC)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 FYDNIKYCQAMAHS-UHFFFAOYSA-N 0.000 claims 1
LNBWGOPHIQPWRI-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C=1C=NNC=1 LNBWGOPHIQPWRI-UHFFFAOYSA-N 0.000 claims 1
SILXUOZMEZPQGK-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-(1h-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=3C=C4C=CNC4=NC=3)=CN=C2C=NC=1C(=O)N(C)C1=CC=C(C#N)C=C1 SILXUOZMEZPQGK-UHFFFAOYSA-N 0.000 claims 1
IINSFLIELSZSIM-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-(2-methylpyridin-4-yl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=NC(C)=C1 IINSFLIELSZSIM-UHFFFAOYSA-N 0.000 claims 1
LIVRSSMLTJQFIG-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-(4-methylphenyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C)C=C1 LIVRSSMLTJQFIG-UHFFFAOYSA-N 0.000 claims 1
UAKNDIAMAVLQOV-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(S(C)(=O)=O)C=C1 UAKNDIAMAVLQOV-UHFFFAOYSA-N 0.000 claims 1
QYDPLIDRIDGAMK-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-(4-phenoxyphenyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1OC1=CC=CC=C1 QYDPLIDRIDGAMK-UHFFFAOYSA-N 0.000 claims 1
MXHKYOCQQCSUSM-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-(5-methylpyridin-2-yl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C)C=N1 MXHKYOCQQCSUSM-UHFFFAOYSA-N 0.000 claims 1
RRXSCDASMYAZAW-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-(5-sulfamoylpyridin-3-yl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CN=CC(S(N)(=O)=O)=C1 RRXSCDASMYAZAW-UHFFFAOYSA-N 0.000 claims 1
HGKJTIOUWOGTKP-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-(6-methylpyridin-3-yl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C)N=C1 HGKJTIOUWOGTKP-UHFFFAOYSA-N 0.000 claims 1
NPEGARIFUIDENJ-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-(6-propoxypyridin-3-yl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=NC(OCCC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 NPEGARIFUIDENJ-UHFFFAOYSA-N 0.000 claims 1
UIFOAMSYBWNGAK-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[2-methyl-4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1C UIFOAMSYBWNGAK-UHFFFAOYSA-N 0.000 claims 1
CNWVMDBECCHABM-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[3-(1h-pyrazol-4-yl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=1)=CC=CC=1C=1C=NNC=1 CNWVMDBECCHABM-UHFFFAOYSA-N 0.000 claims 1
OEGJSVKEIJCBOQ-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=CC(C(F)(F)F)=C1 OEGJSVKEIJCBOQ-UHFFFAOYSA-N 0.000 claims 1
MIGAIZUAPPOYNX-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[4-(1,3,4-oxadiazol-2-yl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=NN=CO1 MIGAIZUAPPOYNX-UHFFFAOYSA-N 0.000 claims 1
WSSLPHYRZXIYKQ-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[4-(1,3,4-thiadiazol-2-yl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=NN=CS1 WSSLPHYRZXIYKQ-UHFFFAOYSA-N 0.000 claims 1
YEUDDPVZLPYOJS-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[4-(1h-pyrazol-5-yl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=CC=NN1 YEUDDPVZLPYOJS-UHFFFAOYSA-N 0.000 claims 1
RCXXNEQBVIMBCW-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[4-(2,2,2-trifluoroethoxy)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(OCC(F)(F)F)C=C1 RCXXNEQBVIMBCW-UHFFFAOYSA-N 0.000 claims 1
DFRNFZILHIUBOA-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[4-(methylamino)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(NC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 DFRNFZILHIUBOA-UHFFFAOYSA-N 0.000 claims 1
SVIYAQDUUGCJJB-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[4-(methylcarbamoyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 SVIYAQDUUGCJJB-UHFFFAOYSA-N 0.000 claims 1
HXYZLABQVDLCRT-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[4-(trifluoromethoxy)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(OC(F)(F)F)C=C1 HXYZLABQVDLCRT-UHFFFAOYSA-N 0.000 claims 1
XAZOWMVYGFASLH-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 XAZOWMVYGFASLH-UHFFFAOYSA-N 0.000 claims 1
SYCBVYFAAKTBTK-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[4-[5-(methylamino)-1,3,4-oxadiazol-2-yl]phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound O1C(NC)=NN=C1C1=CC=C(C=2N3C=C(N=CC3=NC=2)C(=O)N(C)C=2C=CC(=CC=2)C#N)C=C1 SYCBVYFAAKTBTK-UHFFFAOYSA-N 0.000 claims 1
IPMIMBDTROUASX-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[4-[5-(methylamino)-1,3,4-thiadiazol-2-yl]phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound S1C(NC)=NN=C1C1=CC=C(C=2N3C=C(N=CC3=NC=2)C(=O)N(C)C=2C=CC(=CC=2)C#N)C=C1 IPMIMBDTROUASX-UHFFFAOYSA-N 0.000 claims 1
FOOYQDRCPNIAPP-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[5-(2-oxopyrrolidin-1-yl)pyrazin-2-yl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(N=C1)=CN=C1N1CCCC1=O FOOYQDRCPNIAPP-UHFFFAOYSA-N 0.000 claims 1
PQSRAEPEMGQSHA-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[6-(methylamino)pyridin-3-yl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=NC(NC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 PQSRAEPEMGQSHA-UHFFFAOYSA-N 0.000 claims 1
HBEKFDOKZWDQTB-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[6-(methylcarbamoyl)pyridin-3-yl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(=CC=1)C#N)N=C2 HBEKFDOKZWDQTB-UHFFFAOYSA-N 0.000 claims 1
DXRJXEQVNAQRLX-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[6-(trifluoromethyl)pyridin-3-yl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)N=C1 DXRJXEQVNAQRLX-UHFFFAOYSA-N 0.000 claims 1
MIXZDNYUUXDFBX-UHFFFAOYSA-N n-(4-ethoxypyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CCOC1=CC=NC(N(C)C(=O)C=2N=CC3=NC=C(N3C=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 MIXZDNYUUXDFBX-UHFFFAOYSA-N 0.000 claims 1
UJMMLBMTKDHCDE-UHFFFAOYSA-N n-(4-ethylpyridin-2-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CCC1=CC=NC(NC(=O)C=2N=CC3=NC=C(N3C=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 UJMMLBMTKDHCDE-UHFFFAOYSA-N 0.000 claims 1
FZDXHGCJSUGIAE-UHFFFAOYSA-N n-(4-ethylpyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CCC1=CC=NC(N(C)C(=O)C=2N=CC3=NC=C(N3C=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 FZDXHGCJSUGIAE-UHFFFAOYSA-N 0.000 claims 1
KBQJAKUJDHNGBN-UHFFFAOYSA-N n-(4-fluorophenyl)-3-(4-methoxyphenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(F)=CC=1)N=C2 KBQJAKUJDHNGBN-UHFFFAOYSA-N 0.000 claims 1
YHBBZEIERDSUAE-UHFFFAOYSA-N n-(4-fluorophenyl)-n-methyl-3-(4-methylphenyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C)C=C1 YHBBZEIERDSUAE-UHFFFAOYSA-N 0.000 claims 1
RXVRWXPPBNGICT-UHFFFAOYSA-N n-(4-fluorophenyl)-n-methyl-3-[4-(1,3,4-thiadiazol-2-yl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=NN=CS1 RXVRWXPPBNGICT-UHFFFAOYSA-N 0.000 claims 1
YFFOTMRKLOEKME-UHFFFAOYSA-N n-(4-fluorophenyl)-n-methyl-3-[4-(1h-pyrazol-5-yl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=CC=NN1 YFFOTMRKLOEKME-UHFFFAOYSA-N 0.000 claims 1
APVFBIWGNBWDBZ-UHFFFAOYSA-N n-(4-fluorophenyl)-n-methyl-3-[4-(methylcarbamoyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=CC(F)=CC=1)N=C2 APVFBIWGNBWDBZ-UHFFFAOYSA-N 0.000 claims 1
FKCLFZDVWINDCQ-UHFFFAOYSA-N n-(4-fluorophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 FKCLFZDVWINDCQ-UHFFFAOYSA-N 0.000 claims 1
XIBWEZXDRDKYOZ-UHFFFAOYSA-N n-(4-fluorophenyl)-n-methyl-3-[4-[5-(methylamino)-1,3,4-oxadiazol-2-yl]phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound O1C(NC)=NN=C1C1=CC=C(C=2N3C=C(N=CC3=NC=2)C(=O)N(C)C=2C=CC(F)=CC=2)C=C1 XIBWEZXDRDKYOZ-UHFFFAOYSA-N 0.000 claims 1
AMAOIMFDPAVTEY-UHFFFAOYSA-N n-(4-fluoropyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C(F)=CC=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 AMAOIMFDPAVTEY-UHFFFAOYSA-N 0.000 claims 1
ZQUGVPMHIPPVEK-UHFFFAOYSA-N n-(4-methoxyphenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(OC)=CC=C1N(C)C(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 ZQUGVPMHIPPVEK-UHFFFAOYSA-N 0.000 claims 1
NMPTUOBPUMQOSH-UHFFFAOYSA-N n-(4-methoxypyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound COC1=CC=NC(N(C)C(=O)C=2N=CC3=NC=C(N3C=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 NMPTUOBPUMQOSH-UHFFFAOYSA-N 0.000 claims 1
CPKAGFZZGJOBNM-UHFFFAOYSA-N n-(4-methoxypyridin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound COC1=CC=NC=C1N(C)C(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 CPKAGFZZGJOBNM-UHFFFAOYSA-N 0.000 claims 1
GZAQEANFENSCAO-UHFFFAOYSA-N n-(5-bromopyrazin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N=C(Br)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 GZAQEANFENSCAO-UHFFFAOYSA-N 0.000 claims 1
RBQKDSXHDWTDFW-UHFFFAOYSA-N n-(5-bromopyrimidin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound N=1C=C(Br)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 RBQKDSXHDWTDFW-UHFFFAOYSA-N 0.000 claims 1
MEVJFHPZKHNGEI-UHFFFAOYSA-N n-(5-chloro-3-fluoropyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound N=1C=C(Cl)C=C(F)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 MEVJFHPZKHNGEI-UHFFFAOYSA-N 0.000 claims 1
RDGVNZATOZFGEG-UHFFFAOYSA-N n-(5-chloropyrazin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N=C(Cl)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 RDGVNZATOZFGEG-UHFFFAOYSA-N 0.000 claims 1
RQAPJZAGANIJCZ-UHFFFAOYSA-N n-(5-chloropyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 RQAPJZAGANIJCZ-UHFFFAOYSA-N 0.000 claims 1
NBZHQMJVRBQPTB-UHFFFAOYSA-N n-(5-chloropyrimidin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound N=1C=C(Cl)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 NBZHQMJVRBQPTB-UHFFFAOYSA-N 0.000 claims 1
QLXZGYQRNQWDQG-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-3-[4-(difluoromethoxy)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(OC(F)F)C=C1 QLXZGYQRNQWDQG-UHFFFAOYSA-N 0.000 claims 1
WTYFIROJOPGNNG-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-3-[4-(difluoromethyl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)F)C=C1 WTYFIROJOPGNNG-UHFFFAOYSA-N 0.000 claims 1
SHWMRQZUVUWJBI-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-methyl-3-[4-(1h-pyrazol-5-yl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=CC=NN1 SHWMRQZUVUWJBI-UHFFFAOYSA-N 0.000 claims 1
QLKJPWQRDFPKHA-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 QLKJPWQRDFPKHA-UHFFFAOYSA-N 0.000 claims 1
QVPFCCLIVGGJOD-UHFFFAOYSA-N n-(5-cyclobutylpyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C2CCC2)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 QVPFCCLIVGGJOD-UHFFFAOYSA-N 0.000 claims 1
FBNQTXUVAVIKRT-UHFFFAOYSA-N n-(5-cyclopentylpyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C2CCCC2)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 FBNQTXUVAVIKRT-UHFFFAOYSA-N 0.000 claims 1
OFDBRKQHXKXDMB-UHFFFAOYSA-N n-(5-ethylpyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound N1=CC(CC)=CC=C1N(C)C(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 OFDBRKQHXKXDMB-UHFFFAOYSA-N 0.000 claims 1
BGESNLXMPZOOHR-UHFFFAOYSA-N n-(5-fluoropyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 BGESNLXMPZOOHR-UHFFFAOYSA-N 0.000 claims 1
QYDNCLPKJCOYGO-UHFFFAOYSA-N n-(5-methoxypyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound N1=CC(OC)=CC=C1N(C)C(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 QYDNCLPKJCOYGO-UHFFFAOYSA-N 0.000 claims 1
NORGLUWGOFAJEJ-UHFFFAOYSA-N n-(5-methylpyridin-2-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound N1=CC(C)=CC=C1NC(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 NORGLUWGOFAJEJ-UHFFFAOYSA-N 0.000 claims 1
VHRCRVIHQUIPCT-UHFFFAOYSA-N n-(6-bromopyridazin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Br)N=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 VHRCRVIHQUIPCT-UHFFFAOYSA-N 0.000 claims 1
QDPAOYOSTKGHIM-UHFFFAOYSA-N n-(6-bromopyridin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Br)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 QDPAOYOSTKGHIM-UHFFFAOYSA-N 0.000 claims 1
QDTLUNYPPCMQQU-UHFFFAOYSA-N n-(6-chloro-5-methylpyridin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N=C(Cl)C(C)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 QDTLUNYPPCMQQU-UHFFFAOYSA-N 0.000 claims 1
CXLAOJLCXQJFSB-UHFFFAOYSA-N n-(6-chloropyridazin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)N=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 CXLAOJLCXQJFSB-UHFFFAOYSA-N 0.000 claims 1
ONZUAPVVFVTEHH-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-3-(1h-indazol-5-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=3C=C4C=NNC4=CC=3)=CN=C2C=NC=1C(=O)N(C)C1=CC=C(Cl)N=C1 ONZUAPVVFVTEHH-UHFFFAOYSA-N 0.000 claims 1
RVMBEVKZHNRQGL-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-3-(1h-indol-5-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=3C=C4C=CNC4=CC=3)=CN=C2C=NC=1C(=O)N(C)C1=CC=C(Cl)N=C1 RVMBEVKZHNRQGL-UHFFFAOYSA-N 0.000 claims 1
SBSLJYAUIMPKNF-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=3C=C4OCCOC4=CC=3)=CN=C2C=NC=1C(=O)N(C)C1=CC=C(Cl)N=C1 SBSLJYAUIMPKNF-UHFFFAOYSA-N 0.000 claims 1
LFIZZXRFZWRGKN-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-3-(2-fluoro-4-methoxyphenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound FC1=CC(OC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=NC(Cl)=CC=1)N=C2 LFIZZXRFZWRGKN-UHFFFAOYSA-N 0.000 claims 1
DIYGQVLZTFIZKW-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-3-(4-fluorophenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(F)C=C1 DIYGQVLZTFIZKW-UHFFFAOYSA-N 0.000 claims 1
CPQWGPJFQUSQHR-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-3-(4-methoxyphenyl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=NC(Cl)=CC=1)N=C2 CPQWGPJFQUSQHR-UHFFFAOYSA-N 0.000 claims 1
RJUWRRFKKWTLKY-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-3-(6-methoxypyridin-3-yl)-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=NC(OC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=NC(Cl)=CC=1)N=C2 RJUWRRFKKWTLKY-UHFFFAOYSA-N 0.000 claims 1
ARDAGUYNDCZHHJ-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-3-[2-fluoro-4-(trifluoromethyl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1F ARDAGUYNDCZHHJ-UHFFFAOYSA-N 0.000 claims 1
VFBPNQQNDBAOCG-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-3-[3-(dimethylamino)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CN(C)C1=CC=CC(C=2N3C=C(N=CC3=NC=2)C(=O)N(C)C=2C=NC(Cl)=CC=2)=C1 VFBPNQQNDBAOCG-UHFFFAOYSA-N 0.000 claims 1
GPRLZFRRTAUHPO-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-3-[3-fluoro-4-(trifluoromethyl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C(F)=C1 GPRLZFRRTAUHPO-UHFFFAOYSA-N 0.000 claims 1
YMQNAXIOEMYIIF-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-3-[4-(1,1-difluoroethyl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(C)(F)F)C=C1 YMQNAXIOEMYIIF-UHFFFAOYSA-N 0.000 claims 1
HHNKDHIIKQEJDK-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-3-[4-(cyclopropylcarbamoyl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C(=O)NC1CC1 HHNKDHIIKQEJDK-UHFFFAOYSA-N 0.000 claims 1
HSJRFBPCUZOYFZ-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-3-[4-(difluoromethoxy)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(OC(F)F)C=C1 HSJRFBPCUZOYFZ-UHFFFAOYSA-N 0.000 claims 1
QSBCOIHXAZCPLK-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-3-[4-(difluoromethyl)phenyl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)F)C=C1 QSBCOIHXAZCPLK-UHFFFAOYSA-N 0.000 claims 1
NPDBDURRDSIKQD-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-3-[6-(dimethylamino)pyridin-3-yl]-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=NC(N(C)C)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=NC(Cl)=CC=1)N=C2 NPDBDURRDSIKQD-UHFFFAOYSA-N 0.000 claims 1
GPDBKVYGJTXXAR-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-3-ethenyl-n-methylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=C)=CN=C2C=NC=1C(=O)N(C)C1=CC=C(Cl)N=C1 GPDBKVYGJTXXAR-UHFFFAOYSA-N 0.000 claims 1
BUXNGVNCEDDRBA-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-n-methyl-3-(1h-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=3C=C4C=CNC4=NC=3)=CN=C2C=NC=1C(=O)N(C)C1=CC=C(Cl)N=C1 BUXNGVNCEDDRBA-UHFFFAOYSA-N 0.000 claims 1
LPVBRBDPFSRREE-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-n-methyl-3-(4-methylphenyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C)C=C1 LPVBRBDPFSRREE-UHFFFAOYSA-N 0.000 claims 1
HFPBLAWNQJWMOE-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-n-methyl-3-[4-(1h-pyrazol-5-yl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=C1)=CC=C1C1=CC=NN1 HFPBLAWNQJWMOE-UHFFFAOYSA-N 0.000 claims 1
AROSQIAAEUHLQH-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-n-methyl-3-[4-(methylamino)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(NC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=NC(Cl)=CC=1)N=C2 AROSQIAAEUHLQH-UHFFFAOYSA-N 0.000 claims 1
IPHCKTPTVXZCAQ-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 IPHCKTPTVXZCAQ-UHFFFAOYSA-N 0.000 claims 1
HYRSBYJOYMGPSH-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-n-methyl-3-[6-(5-methyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C(C=N1)=CC=C1C1=NN=C(C)O1 HYRSBYJOYMGPSH-UHFFFAOYSA-N 0.000 claims 1
IBUHMLBDXRAOIN-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-n-methyl-3-[6-(methylamino)pyridin-3-yl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=NC(NC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1C=NC(Cl)=CC=1)N=C2 IBUHMLBDXRAOIN-UHFFFAOYSA-N 0.000 claims 1
IZSRMTMOWDEQGQ-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-n-methyl-3-[6-(trifluoromethyl)pyridin-3-yl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)N=C1 IZSRMTMOWDEQGQ-UHFFFAOYSA-N 0.000 claims 1
FCTFZUYTYZKZLI-UHFFFAOYSA-N n-(6-fluoropyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=CC(F)=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 FCTFZUYTYZKZLI-UHFFFAOYSA-N 0.000 claims 1
LHPTUCRDCJNDLC-UHFFFAOYSA-N n-(6-fluoropyridin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 LHPTUCRDCJNDLC-UHFFFAOYSA-N 0.000 claims 1
WMHOQZPQNRGNGG-UHFFFAOYSA-N n-(6-methoxy-5-methylpyridin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=C(C)C(OC)=NC=C1N(C)C(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 WMHOQZPQNRGNGG-UHFFFAOYSA-N 0.000 claims 1
PYXGHXIGSZUPHA-UHFFFAOYSA-N n-(6-methoxypyridazin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound N1=NC(OC)=CC=C1N(C)C(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 PYXGHXIGSZUPHA-UHFFFAOYSA-N 0.000 claims 1
VTFOKQFTALGSTA-UHFFFAOYSA-N n-(6-methoxypyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound COC1=CC=CC(N(C)C(=O)C=2N=CC3=NC=C(N3C=2)C=2C=CC(=CC=2)C(F)(F)F)=N1 VTFOKQFTALGSTA-UHFFFAOYSA-N 0.000 claims 1
MLZMFZHQWPKEJW-UHFFFAOYSA-N n-(6-methoxypyridin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=NC(OC)=CC=C1N(C)C(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 MLZMFZHQWPKEJW-UHFFFAOYSA-N 0.000 claims 1
DFGYYRHXXFUQGC-UHFFFAOYSA-N n-(6-tert-butylpyridin-3-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C(C)(C)C)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 DFGYYRHXXFUQGC-UHFFFAOYSA-N 0.000 claims 1
GNUNZOHPRIPSDC-UHFFFAOYSA-N n-(7-chloro-1,3-benzothiazol-2-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CN=C2N1C=C(C(=O)NC=1SC3=C(Cl)C=CC=C3N=1)N=C2 GNUNZOHPRIPSDC-UHFFFAOYSA-N 0.000 claims 1
BNQSUVQAMQEFSW-UHFFFAOYSA-N n-[(4-cyanophenyl)methyl]-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CN=C2N1C=C(C(=O)NCC=1C=CC(=CC=1)C#N)N=C2 BNQSUVQAMQEFSW-UHFFFAOYSA-N 0.000 claims 1
IJIPUYWECLXUHJ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2C=NC=1C(=O)N(C)CC1=CC=C(F)C=C1 IJIPUYWECLXUHJ-UHFFFAOYSA-N 0.000 claims 1
PUOLJMGZRMAIPA-UHFFFAOYSA-N n-[1-(4-chlorophenyl)ethyl]-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(C)N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 PUOLJMGZRMAIPA-UHFFFAOYSA-N 0.000 claims 1
BDEPMIMISOPMRB-UHFFFAOYSA-N n-[2-(4-fluorophenyl)propan-2-yl]-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(F)C=CC=1C(C)(C)NC(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 BDEPMIMISOPMRB-UHFFFAOYSA-N 0.000 claims 1
GFOUIRFXRSQSCT-UHFFFAOYSA-N n-[2-(difluoromethoxy)phenyl]-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=CC=C(OC(F)F)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 GFOUIRFXRSQSCT-UHFFFAOYSA-N 0.000 claims 1
FGNZIWQMEFVGJE-UHFFFAOYSA-N n-[3-(6-acetamidopyridin-3-yl)imidazo[1,2-a]pyrazin-6-yl]-4-fluoro-n-methylbenzamide Chemical compound C=1N2C(C=3C=NC(NC(C)=O)=CC=3)=CN=C2C=NC=1N(C)C(=O)C1=CC=C(F)C=C1 FGNZIWQMEFVGJE-UHFFFAOYSA-N 0.000 claims 1
SBNIIIXZGDKKLV-UHFFFAOYSA-N n-[4-(aminomethyl)phenyl]-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(CN)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 SBNIIIXZGDKKLV-UHFFFAOYSA-N 0.000 claims 1
UUJNBDNKDBYZLN-UHFFFAOYSA-N n-[4-(difluoromethoxy)phenyl]-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(OC(F)F)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 UUJNBDNKDBYZLN-UHFFFAOYSA-N 0.000 claims 1
HWHADUVVDSRXLQ-UHFFFAOYSA-N n-[5-[6-[(4-cyano-n-methylanilino)methyl]imidazo[1,2-a]pyrazin-3-yl]pyridin-2-yl]acetamide Chemical compound C=1C=C(C#N)C=CC=1N(C)CC(N=CC1=NC=2)=CN1C=2C1=CC=C(NC(C)=O)N=C1 HWHADUVVDSRXLQ-UHFFFAOYSA-N 0.000 claims 1
QTAPGPINKUDGKG-UHFFFAOYSA-N n-[5-[6-[[methyl-(5-methylpyridin-2-yl)amino]methyl]imidazo[1,2-a]pyrazin-3-yl]pyridin-2-yl]acetamide Chemical compound C=1C=C(C)C=NC=1N(C)CC(N=CC1=NC=2)=CN1C=2C1=CC=C(NC(C)=O)N=C1 QTAPGPINKUDGKG-UHFFFAOYSA-N 0.000 claims 1
QOWCPUMCDUWZPY-UHFFFAOYSA-N n-[6-(dimethylamino)pyridin-3-yl]-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=NC(N(C)C)=CC=C1N(C)C(=O)C(N=C1)=CN2C1=NC=C2C1=CC=C(C(F)(F)F)C=C1 QOWCPUMCDUWZPY-UHFFFAOYSA-N 0.000 claims 1
WABRFTIUSSVESL-FQEVSTJZSA-N n-[6-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]pyridin-3-yl]-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound COC[C@@H]1CCCN1C1=CC=C(N(C)C(=O)C=2N=CC3=NC=C(N3C=2)C=2C=CC(=CC=2)C(F)(F)F)C=N1 WABRFTIUSSVESL-FQEVSTJZSA-N 0.000 claims 1
DJYFHCXWYGQSIS-UHFFFAOYSA-N n-[[3-(4-chlorophenyl)imidazo[1,2-a]pyrazin-6-yl]methyl]-4-fluoro-n-methylaniline Chemical compound C=1C=C(F)C=CC=1N(C)CC(N=CC1=NC=2)=CN1C=2C1=CC=C(Cl)C=C1 DJYFHCXWYGQSIS-UHFFFAOYSA-N 0.000 claims 1
LTXHRHSDTNTJPV-UHFFFAOYSA-N n-[[3-[4-(difluoromethoxy)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl]-4-fluoro-n-methylaniline Chemical compound C=1C=C(F)C=CC=1N(C)CC(N=CC1=NC=2)=CN1C=2C1=CC=C(OC(F)F)C=C1 LTXHRHSDTNTJPV-UHFFFAOYSA-N 0.000 claims 1
OJYLXDZZCPEWBL-UHFFFAOYSA-N n-[[3-[4-(difluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]methyl]-n,5-dimethylpyridin-2-amine Chemical compound C=1C=C(C)C=NC=1N(C)CC(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)F)C=C1 OJYLXDZZCPEWBL-UHFFFAOYSA-N 0.000 claims 1
LHMUMRINTZZUBI-UHFFFAOYSA-N n-benzyl-n-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2C=NC=1C(=O)N(C)CC1=CC=CC=C1 LHMUMRINTZZUBI-UHFFFAOYSA-N 0.000 claims 1
VGRJEEWOLOKCRZ-UHFFFAOYSA-N n-methyl-3-[4-(methylcarbamoyl)phenyl]-n-(5-methylpyridin-2-yl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CN=C2N1C=C(C(=O)N(C)C=1N=CC(C)=CC=1)N=C2 VGRJEEWOLOKCRZ-UHFFFAOYSA-N 0.000 claims 1
AOFQZTUUQRFVFX-UHFFFAOYSA-N n-methyl-3-[4-(trifluoromethyl)phenyl]-n-[2-(trifluoromethyl)pyridin-4-yl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=NC(C(F)(F)F)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 AOFQZTUUQRFVFX-UHFFFAOYSA-N 0.000 claims 1
OPUHLJGNYIOVCZ-UHFFFAOYSA-N n-methyl-3-[4-(trifluoromethyl)phenyl]-n-[4-(trifluoromethyl)pyridin-2-yl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C(C(F)(F)F)=CC=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 OPUHLJGNYIOVCZ-UHFFFAOYSA-N 0.000 claims 1
HCAZXOGBBFZEHS-UHFFFAOYSA-N n-methyl-3-[4-(trifluoromethyl)phenyl]-n-[6-(trifluoromethyl)pyridin-3-yl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C(F)(F)F)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 HCAZXOGBBFZEHS-UHFFFAOYSA-N 0.000 claims 1
UNYKGOLQWIOGGC-UHFFFAOYSA-N n-methyl-4-(trifluoromethoxy)-n-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C=1N2C(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2C=NC=1N(C)C(=O)C1=CC=C(OC(F)(F)F)C=C1 UNYKGOLQWIOGGC-UHFFFAOYSA-N 0.000 claims 1
NZYWHDUHHIRKBL-UHFFFAOYSA-N n-methyl-4-(trifluoromethyl)-n-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C=1N2C(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2C=NC=1N(C)C(=O)C1=CC=C(C(F)(F)F)C=C1 NZYWHDUHHIRKBL-UHFFFAOYSA-N 0.000 claims 1
QMSPSHTUEILGGW-UHFFFAOYSA-N n-methyl-6-(trifluoromethyl)-n-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]pyridine-3-carboxamide Chemical compound C=1N2C(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2C=NC=1N(C)C(=O)C1=CC=C(C(F)(F)F)N=C1 QMSPSHTUEILGGW-UHFFFAOYSA-N 0.000 claims 1
LWBPYFFFYSGMEO-UHFFFAOYSA-N n-methyl-n,3-bis[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 LWBPYFFFYSGMEO-UHFFFAOYSA-N 0.000 claims 1
VPJIHUZYBHDABA-UHFFFAOYSA-N n-methyl-n-(1,3-thiazol-2-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound N=1C=CSC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 VPJIHUZYBHDABA-UHFFFAOYSA-N 0.000 claims 1
CBNVZPXNWWJJLV-UHFFFAOYSA-N n-methyl-n-(2-methylpyridin-3-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=CN=C(C)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 CBNVZPXNWWJJLV-UHFFFAOYSA-N 0.000 claims 1
QIPXIGXEKMQOBA-UHFFFAOYSA-N n-methyl-n-(2-methylpyridin-4-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=NC(C)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 QIPXIGXEKMQOBA-UHFFFAOYSA-N 0.000 claims 1
UHNRVMUCUZSGHD-UHFFFAOYSA-N n-methyl-n-(3-methylpyridin-2-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound N=1C=CC=C(C)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 UHNRVMUCUZSGHD-UHFFFAOYSA-N 0.000 claims 1
IDAWHRZMFZHMPZ-UHFFFAOYSA-N n-methyl-n-(4-methylpyridin-3-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N=CC=C(C)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 IDAWHRZMFZHMPZ-UHFFFAOYSA-N 0.000 claims 1
LUNUALPHNYVWAW-UHFFFAOYSA-N n-methyl-n-(4-phenoxyphenyl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 LUNUALPHNYVWAW-UHFFFAOYSA-N 0.000 claims 1
NQDNWMDNJYUQEN-UHFFFAOYSA-N n-methyl-n-(4-phenyl-1,3-thiazol-2-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound N=1C(C=2C=CC=CC=2)=CSC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 NQDNWMDNJYUQEN-UHFFFAOYSA-N 0.000 claims 1
DHCPATURXXODCG-UHFFFAOYSA-N n-methyl-n-(4-sulfamoylphenyl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(S(N)(=O)=O)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 DHCPATURXXODCG-UHFFFAOYSA-N 0.000 claims 1
BHLKJCNHVCUBNR-UHFFFAOYSA-N n-methyl-n-(5-methylpyridin-2-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 BHLKJCNHVCUBNR-UHFFFAOYSA-N 0.000 claims 1
RUXMJYULHGQWLU-UHFFFAOYSA-N n-methyl-n-(5-methylpyridin-3-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N=CC(C)=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 RUXMJYULHGQWLU-UHFFFAOYSA-N 0.000 claims 1
BSZLSGHBVIEAAA-UHFFFAOYSA-N n-methyl-n-(5-methylpyrimidin-2-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound N=1C=C(C)C=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 BSZLSGHBVIEAAA-UHFFFAOYSA-N 0.000 claims 1
MWTCTPPXIWEIHA-UHFFFAOYSA-N n-methyl-n-(6-methylpyridin-2-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=CC(C)=NC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 MWTCTPPXIWEIHA-UHFFFAOYSA-N 0.000 claims 1
FPUJEIGPELVQHM-UHFFFAOYSA-N n-methyl-n-(6-methylpyridin-3-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 FPUJEIGPELVQHM-UHFFFAOYSA-N 0.000 claims 1
BTMGVQARMBPNOO-UHFFFAOYSA-N n-methyl-n-(6-phenylpyridin-3-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(C=2C=CC=CC=2)N=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 BTMGVQARMBPNOO-UHFFFAOYSA-N 0.000 claims 1
KQBBJLRPOYVEFP-UHFFFAOYSA-N n-methyl-n-([1,2,4]triazolo[4,3-a]pyridin-5-yl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=CC2=NN=CN2C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 KQBBJLRPOYVEFP-UHFFFAOYSA-N 0.000 claims 1
JQZLPKFAKGNJIK-UHFFFAOYSA-N n-methyl-n-(pyridin-3-ylmethyl)-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2C=NC=1C(=O)N(C)CC1=CC=CN=C1 JQZLPKFAKGNJIK-UHFFFAOYSA-N 0.000 claims 1
UXEFZEVOJGZMIW-UHFFFAOYSA-N n-methyl-n-[(6-methylpyridin-2-yl)methyl]-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1N2C(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2C=NC=1C(=O)N(C)CC1=CC=CC(C)=N1 UXEFZEVOJGZMIW-UHFFFAOYSA-N 0.000 claims 1
JFGMHRLWDUSASI-UHFFFAOYSA-N n-methyl-n-[2-(trifluoromethoxy)phenyl]-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=CC=C(OC(F)(F)F)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 JFGMHRLWDUSASI-UHFFFAOYSA-N 0.000 claims 1
QERYLSYRPUMMPK-UHFFFAOYSA-N n-methyl-n-[2-(trifluoromethyl)phenyl]-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=CC=C(C(F)(F)F)C=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 QERYLSYRPUMMPK-UHFFFAOYSA-N 0.000 claims 1
DURZQIOIHQFNSG-UHFFFAOYSA-N n-methyl-n-[3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazin-6-yl]pyrimidine-5-carboxamide Chemical compound C=1N2C(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2C=NC=1N(C)C(=O)C1=CN=CN=C1 DURZQIOIHQFNSG-UHFFFAOYSA-N 0.000 claims 1
KHWTVTQKLJLWMI-UHFFFAOYSA-N n-methyl-n-[4-(trifluoromethoxy)phenyl]-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound C=1C=C(OC(F)(F)F)C=CC=1N(C)C(=O)C(N=CC1=NC=2)=CN1C=2C1=CC=C(C(F)(F)F)C=C1 KHWTVTQKLJLWMI-UHFFFAOYSA-N 0.000 claims 1
BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 claims 1
GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
229960005179 primaquine Drugs 0.000 claims 1
INDBQLZJXZLFIT-UHFFFAOYSA-N primaquine Chemical compound N1=CC=CC2=CC(OC)=CC(NC(C)CCCN)=C21 INDBQLZJXZLFIT-UHFFFAOYSA-N 0.000 claims 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 claims 1
229960005385 proguanil Drugs 0.000 claims 1
DJUFPMUQJKWIJB-UHFFFAOYSA-N pyronaridine Chemical compound C12=NC(OC)=CC=C2N=C2C=C(Cl)C=CC2=C1NC(C=C(CN1CCCC1)C=1O)=CC=1CN1CCCC1 DJUFPMUQJKWIJB-UHFFFAOYSA-N 0.000 claims 1
229950011262 pyronaridine Drugs 0.000 claims 1
GPKJTRJOBQGKQK-UHFFFAOYSA-N quinacrine Chemical compound C1=C(OC)C=C2C(NC(C)CCCN(CC)CC)=C(C=CC(Cl)=C3)C3=NC2=C1 GPKJTRJOBQGKQK-UHFFFAOYSA-N 0.000 claims 1
229960001404 quinidine Drugs 0.000 claims 1
229960000948 quinine Drugs 0.000 claims 1
229940124530 sulfonamide Drugs 0.000 claims 1
150000003456 sulfonamides Chemical class 0.000 claims 1
IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 claims 1
229960001082 trimethoprim Drugs 0.000 claims 1

JP2015543098A 2012-11-19 2013-11-18 寄生虫病の処置のための化合物および組成物 Pending JP2016500073A (ja)