KR20100055464A - 오렉신 길항제로서의 1,2-디아미도-에틸렌 유도체 - Google Patents
오렉신 길항제로서의 1,2-디아미도-에틸렌 유도체 Download PDFInfo
- Publication number
- KR20100055464A KR20100055464A KR1020107005493A KR20107005493A KR20100055464A KR 20100055464 A KR20100055464 A KR 20100055464A KR 1020107005493 A KR1020107005493 A KR 1020107005493A KR 20107005493 A KR20107005493 A KR 20107005493A KR 20100055464 A KR20100055464 A KR 20100055464A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- thiazole
- amino
- carboxylic acid
- carbonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 102000002512 Orexin Human genes 0.000 title description 12
- 108060005714 orexin Proteins 0.000 title description 12
- 239000005557 antagonist Substances 0.000 title description 6
- 239000003814 drug Substances 0.000 claims abstract description 14
- -1 bromo, cyclopropyl Chemical group 0.000 claims description 294
- VSQMBZXCDDTZAF-UHFFFAOYSA-N 6-methylimidazo[2,1-b][1,3]thiazole-5-carboxylic acid Chemical compound S1C=CN2C(C(O)=O)=C(C)N=C21 VSQMBZXCDDTZAF-UHFFFAOYSA-N 0.000 claims description 139
- 150000001875 compounds Chemical class 0.000 claims description 73
- IUPHMHDVSPSLME-UHFFFAOYSA-N 2-methyl-5-phenyl-1,3-thiazole-4-carboxylic acid Chemical compound S1C(C)=NC(C(O)=O)=C1C1=CC=CC=C1 IUPHMHDVSPSLME-UHFFFAOYSA-N 0.000 claims description 64
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 43
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 36
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- JWRKIQPISSTIRN-UHFFFAOYSA-N N-[2-(cyclopropylmethylamino)ethyl]-1-benzofuran-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCCNCC1CC1 JWRKIQPISSTIRN-UHFFFAOYSA-N 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- FDRPXJYBJSEVLB-UHFFFAOYSA-N N-[2-(cyclopropylamino)ethyl]-1-benzofuran-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCCNC1CC1 FDRPXJYBJSEVLB-UHFFFAOYSA-N 0.000 claims description 19
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 16
- 208000011580 syndromic disease Diseases 0.000 claims description 14
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 12
- 208000020016 psychiatric disease Diseases 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000623 heterocyclic group Chemical class 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 208000019116 sleep disease Diseases 0.000 claims description 9
- IXJZJGOHTCDPBX-UHFFFAOYSA-N 2-amino-5-(3-fluorophenyl)-1,3-thiazole-4-carboxylic acid Chemical compound S1C(N)=NC(C(O)=O)=C1C1=CC=CC(F)=C1 IXJZJGOHTCDPBX-UHFFFAOYSA-N 0.000 claims description 8
- SIZFESNSRFIQCK-UHFFFAOYSA-N 2-amino-5-(3-methoxyphenyl)-1,3-thiazole-4-carboxylic acid Chemical compound COC1=CC=CC(C2=C(N=C(N)S2)C(O)=O)=C1 SIZFESNSRFIQCK-UHFFFAOYSA-N 0.000 claims description 8
- ODCOWPJBSKLCIC-UHFFFAOYSA-N 5-(2-fluorophenyl)-2-methyl-1,3-thiazole-4-carboxylic acid Chemical compound S1C(C)=NC(C(O)=O)=C1C1=CC=CC=C1F ODCOWPJBSKLCIC-UHFFFAOYSA-N 0.000 claims description 8
- GCBMFDPCVMRYRN-UHFFFAOYSA-N 5-(3-fluorophenyl)-2-methyl-1,3-thiazole-4-carboxylic acid Chemical compound S1C(C)=NC(C(O)=O)=C1C1=CC=CC(F)=C1 GCBMFDPCVMRYRN-UHFFFAOYSA-N 0.000 claims description 8
- IKMJWPHKFSSZGV-UHFFFAOYSA-N 5-(3-methoxyphenyl)-2-methyl-1,3-thiazole-4-carboxylic acid Chemical compound COC1=CC=CC(C2=C(N=C(C)S2)C(O)=O)=C1 IKMJWPHKFSSZGV-UHFFFAOYSA-N 0.000 claims description 8
- 208000012902 Nervous system disease Diseases 0.000 claims description 8
- 208000025966 Neurological disease Diseases 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- FAQZRBHUKFXVLO-UHFFFAOYSA-N 2-amino-5-(4-fluorophenyl)-1,3-thiazole-4-carboxylic acid Chemical compound S1C(N)=NC(C(O)=O)=C1C1=CC=C(F)C=C1 FAQZRBHUKFXVLO-UHFFFAOYSA-N 0.000 claims description 7
- 208000010877 cognitive disease Diseases 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000004565 2,3-dihydrobenzofuran-4-yl group Chemical group O1CCC2=C1C=CC=C2* 0.000 claims description 5
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 230000035622 drinking Effects 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 235000005686 eating Nutrition 0.000 claims description 4
- 230000007937 eating Effects 0.000 claims description 4
- 125000004245 indazol-3-yl group Chemical group [H]N1N=C(*)C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 4
- 125000004254 isoquinolin-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C(*)=N1 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- PDYQJEHUHVAGQX-UHFFFAOYSA-N 2-amino-5-(3-chlorophenyl)-n-(cyclopropylmethyl)-n-[2-[(1-methylindazole-3-carbonyl)amino]ethyl]-1,3-thiazole-4-carboxamide Chemical compound C12=CC=CC=C2N(C)N=C1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=C(Cl)C=CC=1)CC1CC1 PDYQJEHUHVAGQX-UHFFFAOYSA-N 0.000 claims description 3
- CAUBOFJBXMTYRS-UHFFFAOYSA-N 2-amino-5-(3-chlorophenyl)-n-cyclopropyl-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC(Cl)=CC=1C=1SC(N)=NC=1C(=O)N(CCNC(=O)C=1C=2OCCOC=2C=CC=1)C1CC1 CAUBOFJBXMTYRS-UHFFFAOYSA-N 0.000 claims description 3
- ZRNNIUYEZBKUJU-UHFFFAOYSA-N 2-amino-5-(3-chlorophenyl)-n-cyclopropyl-n-[2-[(1-methylindazole-3-carbonyl)amino]ethyl]-1,3-thiazole-4-carboxamide Chemical compound C12=CC=CC=C2N(C)N=C1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=C(Cl)C=CC=1)C1CC1 ZRNNIUYEZBKUJU-UHFFFAOYSA-N 0.000 claims description 3
- CWASEUYAUQXDAM-UHFFFAOYSA-N 2-amino-n-(cyclopropylmethyl)-5-(3-fluorophenyl)-n-[2-[(1-methylindazole-3-carbonyl)amino]ethyl]-1,3-thiazole-4-carboxamide Chemical compound C12=CC=CC=C2N(C)N=C1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=C(F)C=CC=1)CC1CC1 CWASEUYAUQXDAM-UHFFFAOYSA-N 0.000 claims description 3
- ITXUKUPAAVVJGH-UHFFFAOYSA-N 2-amino-n-(cyclopropylmethyl)-5-(3-methoxyphenyl)-n-[2-[(1-methylindazole-3-carbonyl)amino]ethyl]-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(N)S2)C(=O)N(CCNC(=O)C=2C3=CC=CC=C3N(C)N=2)CC2CC2)=C1 ITXUKUPAAVVJGH-UHFFFAOYSA-N 0.000 claims description 3
- SBNTWASSQZTQKK-UHFFFAOYSA-N 2-amino-n-(cyclopropylmethyl)-5-(4-fluorophenyl)-n-[2-[(1-methylindazole-3-carbonyl)amino]ethyl]-1,3-thiazole-4-carboxamide Chemical compound C12=CC=CC=C2N(C)N=C1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=CC(F)=CC=1)CC1CC1 SBNTWASSQZTQKK-UHFFFAOYSA-N 0.000 claims description 3
- NCARDYKBBICTQK-UHFFFAOYSA-N 2-amino-n-(cyclopropylmethyl)-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-(3-fluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC(F)=CC=1C=1SC(N)=NC=1C(=O)N(CCNC(=O)C=1C=2OCCOC=2C=CC=1)CC1CC1 NCARDYKBBICTQK-UHFFFAOYSA-N 0.000 claims description 3
- UWBFUSPPTLQBPD-UHFFFAOYSA-N 2-amino-n-(cyclopropylmethyl)-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-(3-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(N)S2)C(=O)N(CCNC(=O)C=2C=3OCCOC=3C=CC=2)CC2CC2)=C1 UWBFUSPPTLQBPD-UHFFFAOYSA-N 0.000 claims description 3
- BQJWEYWKNLDAPB-UHFFFAOYSA-N 2-amino-n-(cyclopropylmethyl)-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-(3-methylphenyl)-1,3-thiazole-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N)S2)C(=O)N(CCNC(=O)C=2C=3OCCOC=3C=CC=2)CC2CC2)=C1 BQJWEYWKNLDAPB-UHFFFAOYSA-N 0.000 claims description 3
- UKOUMUHYGQMLIO-UHFFFAOYSA-N 2-amino-n-(cyclopropylmethyl)-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(N)=NC=1C(=O)N(CCNC(=O)C=1C=2OCCOC=2C=CC=1)CC1CC1 UKOUMUHYGQMLIO-UHFFFAOYSA-N 0.000 claims description 3
- KFZUEUTXTYWHSU-UHFFFAOYSA-N 2-amino-n-(cyclopropylmethyl)-n-[2-[(1-methylindazole-3-carbonyl)amino]ethyl]-5-(3-methylphenyl)-1,3-thiazole-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N)S2)C(=O)N(CCNC(=O)C=2C3=CC=CC=C3N(C)N=2)CC2CC2)=C1 KFZUEUTXTYWHSU-UHFFFAOYSA-N 0.000 claims description 3
- VTMNKCJAAVEVDL-UHFFFAOYSA-N 2-amino-n-(cyclopropylmethyl)-n-[2-[(1-methylindazole-3-carbonyl)amino]ethyl]-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C12=CC=CC=C2N(C)N=C1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=CC=CC=1)CC1CC1 VTMNKCJAAVEVDL-UHFFFAOYSA-N 0.000 claims description 3
- QYGHLZVXPOWBFD-UHFFFAOYSA-N 2-amino-n-[2-(1-benzofuran-4-carbonylamino)ethyl]-5-(3-chlorophenyl)-n-(cyclopropylmethyl)-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC(Cl)=CC=1C=1SC(N)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1CC1 QYGHLZVXPOWBFD-UHFFFAOYSA-N 0.000 claims description 3
- YRDRCCXGCCHGBQ-UHFFFAOYSA-N 2-amino-n-[2-(1-benzofuran-4-carbonylamino)ethyl]-5-(3-chlorophenyl)-n-cyclopropyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC(Cl)=CC=1C=1SC(N)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)C1CC1 YRDRCCXGCCHGBQ-UHFFFAOYSA-N 0.000 claims description 3
- LJMVOXTUQBXBJN-UHFFFAOYSA-N 2-amino-n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-(cyclopropylmethyl)-5-(3-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(N)S2)C(=O)N(CCNC(=O)C=2C=3C=COC=3C=CC=2)CC2CC2)=C1 LJMVOXTUQBXBJN-UHFFFAOYSA-N 0.000 claims description 3
- SCBLREZNXOORTB-UHFFFAOYSA-N 2-amino-n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-(cyclopropylmethyl)-5-(3-methylphenyl)-1,3-thiazole-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N)S2)C(=O)N(CCNC(=O)C=2C=3C=COC=3C=CC=2)CC2CC2)=C1 SCBLREZNXOORTB-UHFFFAOYSA-N 0.000 claims description 3
- UNGCRHHRSKFQAD-UHFFFAOYSA-N 2-amino-n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-(cyclopropylmethyl)-5-(4-fluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(F)C=CC=1C=1SC(N)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1CC1 UNGCRHHRSKFQAD-UHFFFAOYSA-N 0.000 claims description 3
- RFHDAVOBXGDHQR-UHFFFAOYSA-N 2-amino-n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-(cyclopropylmethyl)-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(N)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1CC1 RFHDAVOBXGDHQR-UHFFFAOYSA-N 0.000 claims description 3
- AECFLPPHWMCCTN-UHFFFAOYSA-N 2-amino-n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-cyclopropyl-5-(3-fluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC(F)=CC=1C=1SC(N)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)C1CC1 AECFLPPHWMCCTN-UHFFFAOYSA-N 0.000 claims description 3
- AIMKCDGVMZVNRX-UHFFFAOYSA-N 2-amino-n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-cyclopropyl-5-(3-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(N)S2)C(=O)N(CCNC(=O)C=2C=3C=COC=3C=CC=2)C2CC2)=C1 AIMKCDGVMZVNRX-UHFFFAOYSA-N 0.000 claims description 3
- PIHKEMMFROEAKB-UHFFFAOYSA-N 2-amino-n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-cyclopropyl-5-(3-methylphenyl)-1,3-thiazole-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N)S2)C(=O)N(CCNC(=O)C=2C=3C=COC=3C=CC=2)C2CC2)=C1 PIHKEMMFROEAKB-UHFFFAOYSA-N 0.000 claims description 3
- ZOOUIDXMVWCCDQ-UHFFFAOYSA-N 2-amino-n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-cyclopropyl-5-(4-fluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(F)C=CC=1C=1SC(N)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)C1CC1 ZOOUIDXMVWCCDQ-UHFFFAOYSA-N 0.000 claims description 3
- BOKSKKBCKBAJIW-UHFFFAOYSA-N 2-amino-n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-cyclopropyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(N)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)C1CC1 BOKSKKBCKBAJIW-UHFFFAOYSA-N 0.000 claims description 3
- QCEDICSIPLCTQA-UHFFFAOYSA-N 2-amino-n-cyclopropyl-5-(3-fluorophenyl)-n-[2-[(1-methylindazole-3-carbonyl)amino]ethyl]-1,3-thiazole-4-carboxamide Chemical compound C12=CC=CC=C2N(C)N=C1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=C(F)C=CC=1)C1CC1 QCEDICSIPLCTQA-UHFFFAOYSA-N 0.000 claims description 3
- NEYUVURBORHCCB-UHFFFAOYSA-N 2-amino-n-cyclopropyl-5-(3-methoxyphenyl)-n-[2-[(1-methylindazole-3-carbonyl)amino]ethyl]-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(N)S2)C(=O)N(CCNC(=O)C=2C3=CC=CC=C3N(C)N=2)C2CC2)=C1 NEYUVURBORHCCB-UHFFFAOYSA-N 0.000 claims description 3
- NPDLUJPOROCDCH-UHFFFAOYSA-N 2-amino-n-cyclopropyl-5-(4-fluorophenyl)-n-[2-[(1-methylindazole-3-carbonyl)amino]ethyl]-1,3-thiazole-4-carboxamide Chemical compound C12=CC=CC=C2N(C)N=C1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=CC(F)=CC=1)C1CC1 NPDLUJPOROCDCH-UHFFFAOYSA-N 0.000 claims description 3
- BJMVYNZUIQIHAE-UHFFFAOYSA-N 2-amino-n-cyclopropyl-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-(3-methylphenyl)-1,3-thiazole-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N)S2)C(=O)N(CCNC(=O)C=2C=3OCCOC=3C=CC=2)C2CC2)=C1 BJMVYNZUIQIHAE-UHFFFAOYSA-N 0.000 claims description 3
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- QXJRYGFUFBZHPF-UHFFFAOYSA-N 2-bromo-n-(cyclopropylmethyl)-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-(4-methylphenyl)-1,3-thiazole-4-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(C(=O)N(CCNC(=O)C=2C=3OCCOC=3C=CC=2)CC2CC2)N=C(Br)S1 QXJRYGFUFBZHPF-UHFFFAOYSA-N 0.000 claims description 3
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- FGSJWXZPEJMKLR-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-2-cyclopropyl-n-(cyclopropylmethyl)-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCCN(C(=O)C1=C(SC(=N1)C1CC1)C=1C=CC=CC=1)CC1CC1 FGSJWXZPEJMKLR-UHFFFAOYSA-N 0.000 claims description 3
- DNIRMUITSGSEBQ-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-2-methyl-5-phenyl-n-(2-phenylethyl)-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CCC1=CC=CC=C1 DNIRMUITSGSEBQ-UHFFFAOYSA-N 0.000 claims description 3
- VEERWIQYZQSXKM-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-2-methyl-5-phenyl-n-(3-phenylpropyl)-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CCCC1=CC=CC=C1 VEERWIQYZQSXKM-UHFFFAOYSA-N 0.000 claims description 3
- LIWSOLYYTOKZNY-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-2-methyl-5-phenyl-n-[[4-(trifluoromethyl)phenyl]methyl]-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1=CC=C(C(F)(F)F)C=C1 LIWSOLYYTOKZNY-UHFFFAOYSA-N 0.000 claims description 3
- PYRJKYUMWDFJCT-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-2-methyl-n-(2-methylpropyl)-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCCN(CC(C)C)C(=O)C=1N=C(C)SC=1C1=CC=CC=C1 PYRJKYUMWDFJCT-UHFFFAOYSA-N 0.000 claims description 3
- RTZNPIUKKMHTIX-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-5-(3-cyanophenyl)-n-(cyclopropylmethyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC(C#N)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1CC1 RTZNPIUKKMHTIX-UHFFFAOYSA-N 0.000 claims description 3
- CNAAVVJXNOVWCH-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-5-(3-cyanophenyl)-n-cyclopropyl-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC(C#N)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)C1CC1 CNAAVVJXNOVWCH-UHFFFAOYSA-N 0.000 claims description 3
- KDPGVDSGICDDIM-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-5-(4-chlorophenyl)-n-(cyclopropylmethyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1CC1 KDPGVDSGICDDIM-UHFFFAOYSA-N 0.000 claims description 3
- FYDNIEBVGGRTMP-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-5-(4-chlorophenyl)-n-cyclopropyl-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)C1CC1 FYDNIEBVGGRTMP-UHFFFAOYSA-N 0.000 claims description 3
- NYJWBAXCKUDVAJ-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-5-(4-fluorophenyl)-n,2-dimethyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCCN(C)C(=O)C=1N=C(C)SC=1C1=CC=C(F)C=C1 NYJWBAXCKUDVAJ-UHFFFAOYSA-N 0.000 claims description 3
- ABCQPLWHTAKBON-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n,2-dicyclopropyl-5-(3-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(S2)C2CC2)C(=O)N(CCNC(=O)C=2C=3C=COC=3C=CC=2)C2CC2)=C1 ABCQPLWHTAKBON-UHFFFAOYSA-N 0.000 claims description 3
- ROMVBRXCYZXSGP-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n,2-dicyclopropyl-5-(3-methylphenyl)-1,3-thiazole-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(S2)C2CC2)C(=O)N(CCNC(=O)C=2C=3C=COC=3C=CC=2)C2CC2)=C1 ROMVBRXCYZXSGP-UHFFFAOYSA-N 0.000 claims description 3
- LZARJVBABOVZIH-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n,2-dicyclopropyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCCN(C(=O)C1=C(SC(=N1)C1CC1)C=1C=CC=CC=1)C1CC1 LZARJVBABOVZIH-UHFFFAOYSA-N 0.000 claims description 3
- FUVZPTKOFNKEJB-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n,2-dimethyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCCN(C)C(=O)C=1N=C(C)SC=1C1=CC=CC=C1 FUVZPTKOFNKEJB-UHFFFAOYSA-N 0.000 claims description 3
- RAJRGIUOYNWFOA-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-(3,3-dimethylbutyl)-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound S1C(C)=NC(C(=O)N(CCNC(=O)C=2C=3C=COC=3C=CC=2)CCC(C)(C)C)=C1C1=CC=CC=C1 RAJRGIUOYNWFOA-UHFFFAOYSA-N 0.000 claims description 3
- LFHZKWLXPIQFDZ-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-(cyclohexylmethyl)-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1CCCCC1 LFHZKWLXPIQFDZ-UHFFFAOYSA-N 0.000 claims description 3
- PZAGFEISIWHDQP-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-(cyclopropylmethyl)-2-methyl-5-(4-methylphenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(C)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1CC1 PZAGFEISIWHDQP-UHFFFAOYSA-N 0.000 claims description 3
- DMGASQNATOXBQU-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-(cyclopropylmethyl)-2-methyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1CC1 DMGASQNATOXBQU-UHFFFAOYSA-N 0.000 claims description 3
- PGXUCBJIQFWJBO-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-(cyclopropylmethyl)-2-methyl-5-[4-(trifluoromethyl)phenyl]-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1CC1 PGXUCBJIQFWJBO-UHFFFAOYSA-N 0.000 claims description 3
- UVVMHIRRYXGGIQ-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-(cyclopropylmethyl)-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1CC1 UVVMHIRRYXGGIQ-UHFFFAOYSA-N 0.000 claims description 3
- FQAYKYOIIQMUNQ-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-(cyclopropylmethyl)-5-(2-fluorophenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=C(F)C=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1CC1 FQAYKYOIIQMUNQ-UHFFFAOYSA-N 0.000 claims description 3
- STRXNSWVBWCYRZ-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-(cyclopropylmethyl)-5-(3,4-dimethylphenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(C)C(C)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1CC1 STRXNSWVBWCYRZ-UHFFFAOYSA-N 0.000 claims description 3
- DGTUAXVECFTQAV-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-(cyclopropylmethyl)-5-(3-fluorophenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC(F)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1CC1 DGTUAXVECFTQAV-UHFFFAOYSA-N 0.000 claims description 3
- XFSWAPSCJCPCIN-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-(cyclopropylmethyl)-5-(3-methoxyphenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(C)S2)C(=O)N(CCNC(=O)C=2C=3C=COC=3C=CC=2)CC2CC2)=C1 XFSWAPSCJCPCIN-UHFFFAOYSA-N 0.000 claims description 3
- CIYYQKOMGUQNOO-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-[(4-fluorophenyl)methyl]-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1=CC=C(F)C=C1 CIYYQKOMGUQNOO-UHFFFAOYSA-N 0.000 claims description 3
- NTCKTGFPEYKLGT-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-benzyl-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1=CC=CC=C1 NTCKTGFPEYKLGT-UHFFFAOYSA-N 0.000 claims description 3
- FCNWEWUKESWWTC-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-benzyl-5-(4-fluorophenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(F)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1=CC=CC=C1 FCNWEWUKESWWTC-UHFFFAOYSA-N 0.000 claims description 3
- CPEKKIOKMGZYOS-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-cyclopropyl-2-methyl-5-(4-methylphenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(C)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)C1CC1 CPEKKIOKMGZYOS-UHFFFAOYSA-N 0.000 claims description 3
- NMEBPGFWNGTBJW-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-cyclopropyl-2-methyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)C1CC1 NMEBPGFWNGTBJW-UHFFFAOYSA-N 0.000 claims description 3
- MUGHFDXVWNNCLK-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-cyclopropyl-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)C1CC1 MUGHFDXVWNNCLK-UHFFFAOYSA-N 0.000 claims description 3
- NNFKAQHBAYIZON-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-cyclopropyl-5-(2-fluorophenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=C(F)C=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)C1CC1 NNFKAQHBAYIZON-UHFFFAOYSA-N 0.000 claims description 3
- MOLKIGRHAWJIJU-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-cyclopropyl-5-(3,4-dimethylphenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(C)C(C)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)C1CC1 MOLKIGRHAWJIJU-UHFFFAOYSA-N 0.000 claims description 3
- XVTBYLJWGGRNMR-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-cyclopropyl-5-(3-fluorophenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC(F)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)C1CC1 XVTBYLJWGGRNMR-UHFFFAOYSA-N 0.000 claims description 3
- FXKAYKKAQGOCTL-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-cyclopropyl-5-(3-methoxyphenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(C)S2)C(=O)N(CCNC(=O)C=2C=3C=COC=3C=CC=2)C2CC2)=C1 FXKAYKKAQGOCTL-UHFFFAOYSA-N 0.000 claims description 3
- HFDWDSPIXFAKSX-UHFFFAOYSA-N n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-2-methyl-5-phenyl-n-(3-phenylpropyl)-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2OCCOC=2C=CC=1)CCCC1=CC=CC=C1 HFDWDSPIXFAKSX-UHFFFAOYSA-N 0.000 claims description 3
- IXWPDBHGEQPSFL-UHFFFAOYSA-N n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-2-methyl-5-phenyl-n-[[4-(trifluoromethyl)phenyl]methyl]-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2OCCOC=2C=CC=1)CC1=CC=C(C(F)(F)F)C=C1 IXWPDBHGEQPSFL-UHFFFAOYSA-N 0.000 claims description 3
- INIGVKRMICCJLA-UHFFFAOYSA-N n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-2-methyl-n-(2-methylpropyl)-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2OCCOC=2C=1C(=O)NCCN(CC(C)C)C(=O)C=1N=C(C)SC=1C1=CC=CC=C1 INIGVKRMICCJLA-UHFFFAOYSA-N 0.000 claims description 3
- DFJJXDNSVVZOIH-UHFFFAOYSA-N n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-n,2-dimethyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical class C=1C=CC=2OCCOC=2C=1C(=O)NCCN(C)C(=O)C=1N=C(C)SC=1C1=CC=CC=C1 DFJJXDNSVVZOIH-UHFFFAOYSA-N 0.000 claims description 3
- QNVHVWLPZXUBHM-UHFFFAOYSA-N n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-n-(3,3-dimethylbutyl)-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound S1C(C)=NC(C(=O)N(CCNC(=O)C=2C=3OCCOC=3C=CC=2)CCC(C)(C)C)=C1C1=CC=CC=C1 QNVHVWLPZXUBHM-UHFFFAOYSA-N 0.000 claims description 3
- KRQYNEARPNJSMY-UHFFFAOYSA-N n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-n-[(4-fluorophenyl)methyl]-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2OCCOC=2C=CC=1)CC1=CC=C(F)C=C1 KRQYNEARPNJSMY-UHFFFAOYSA-N 0.000 claims description 3
- MCGPAIULRMBJAY-UHFFFAOYSA-N n-[2-(2,3-dihydro-1-benzofuran-7-carbonylamino)ethyl]-5-(4-fluorophenyl)-n,2-dimethyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2CCOC=2C=1C(=O)NCCN(C)C(=O)C=1N=C(C)SC=1C1=CC=C(F)C=C1 MCGPAIULRMBJAY-UHFFFAOYSA-N 0.000 claims description 3
- KYQXOHORPJBSEX-UHFFFAOYSA-N n-[2-[(2-amino-5-phenyl-1,3-thiazole-4-carbonyl)-(cyclopropylmethyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=CC=CC=1)CC1CC1 KYQXOHORPJBSEX-UHFFFAOYSA-N 0.000 claims description 3
- OLXMMJKXONHJFB-UHFFFAOYSA-N n-[2-[(2-amino-5-phenyl-1,3-thiazole-4-carbonyl)-cyclopropylamino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical class CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=CC=CC=1)C1CC1 OLXMMJKXONHJFB-UHFFFAOYSA-N 0.000 claims description 3
- WCTBSLBBHDZLFX-UHFFFAOYSA-N n-[2-[(4-fluorophenyl)methyl-(2-methyl-5-phenyl-1,3-thiazole-4-carbonyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1N2C=CSC2=NC=1C)CC1=CC=C(F)C=C1 WCTBSLBBHDZLFX-UHFFFAOYSA-N 0.000 claims description 3
- NMVMKCSZWUKXLS-UHFFFAOYSA-N n-[2-[[2-amino-5-(3-chlorophenyl)-1,3-thiazole-4-carbonyl]-(cyclopropylmethyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=C(Cl)C=CC=1)CC1CC1 NMVMKCSZWUKXLS-UHFFFAOYSA-N 0.000 claims description 3
- HUMGWROQIQYZGY-UHFFFAOYSA-N n-[2-[[2-amino-5-(3-chlorophenyl)-1,3-thiazole-4-carbonyl]-cyclopropylamino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=C(Cl)C=CC=1)C1CC1 HUMGWROQIQYZGY-UHFFFAOYSA-N 0.000 claims description 3
- RRAGLQQTNWLUKD-UHFFFAOYSA-N n-[2-[[2-amino-5-(3-fluorophenyl)-1,3-thiazole-4-carbonyl]-(cyclopropylmethyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=C(F)C=CC=1)CC1CC1 RRAGLQQTNWLUKD-UHFFFAOYSA-N 0.000 claims description 3
- INVVQYFFGBUMSX-UHFFFAOYSA-N n-[2-[[2-amino-5-(3-fluorophenyl)-1,3-thiazole-4-carbonyl]-cyclopropylamino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=C(F)C=CC=1)C1CC1 INVVQYFFGBUMSX-UHFFFAOYSA-N 0.000 claims description 3
- YKRXFGWWZMYBDY-UHFFFAOYSA-N n-[2-[[2-amino-5-(3-methoxyphenyl)-1,3-thiazole-4-carbonyl]-(cyclopropylmethyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(N)S2)C(=O)N(CCNC(=O)C=2N3C=CSC3=NC=2C)CC2CC2)=C1 YKRXFGWWZMYBDY-UHFFFAOYSA-N 0.000 claims description 3
- IJZNLQBBKTZZJP-UHFFFAOYSA-N n-[2-[[2-amino-5-(3-methoxyphenyl)-1,3-thiazole-4-carbonyl]-cyclopropylamino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(N)S2)C(=O)N(CCNC(=O)C=2N3C=CSC3=NC=2C)C2CC2)=C1 IJZNLQBBKTZZJP-UHFFFAOYSA-N 0.000 claims description 3
- VNQVWCVAGJKTPZ-UHFFFAOYSA-N n-[2-[[2-amino-5-(3-methylphenyl)-1,3-thiazole-4-carbonyl]-(cyclopropylmethyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=C(C)C=CC=1)CC1CC1 VNQVWCVAGJKTPZ-UHFFFAOYSA-N 0.000 claims description 3
- OJPPEHNBHLHZLA-UHFFFAOYSA-N n-[2-[[2-amino-5-(3-methylphenyl)-1,3-thiazole-4-carbonyl]-cyclopropylamino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=C(C)C=CC=1)C1CC1 OJPPEHNBHLHZLA-UHFFFAOYSA-N 0.000 claims description 3
- ATXRHKFXKQFTDJ-UHFFFAOYSA-N n-[2-[[2-amino-5-(4-fluorophenyl)-1,3-thiazole-4-carbonyl]-(cyclopropylmethyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=CC(F)=CC=1)CC1CC1 ATXRHKFXKQFTDJ-UHFFFAOYSA-N 0.000 claims description 3
- AYUNIWHLXGNSJM-UHFFFAOYSA-N n-[2-[[2-amino-5-(4-fluorophenyl)-1,3-thiazole-4-carbonyl]-cyclopropylamino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C1=C(SC(N)=N1)C=1C=CC(F)=CC=1)C1CC1 AYUNIWHLXGNSJM-UHFFFAOYSA-N 0.000 claims description 3
- VAXJYMBLYMBBPJ-UHFFFAOYSA-N n-[2-[[2-bromo-5-(3-methoxyphenyl)-1,3-thiazole-4-carbonyl]-(cyclopropylmethyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(Br)S2)C(=O)N(CCNC(=O)C=2N3C=CSC3=NC=2C)CC2CC2)=C1 VAXJYMBLYMBBPJ-UHFFFAOYSA-N 0.000 claims description 3
- XTEVYLQPEHPSJY-UHFFFAOYSA-N n-[2-[[2-bromo-5-(3-methoxyphenyl)-1,3-thiazole-4-carbonyl]-cyclopropylamino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(Br)S2)C(=O)N(CCNC(=O)C=2N3C=CSC3=NC=2C)C2CC2)=C1 XTEVYLQPEHPSJY-UHFFFAOYSA-N 0.000 claims description 3
- WNPWJUUJTFRWHC-UHFFFAOYSA-N n-[2-[[2-bromo-5-(4-methylphenyl)-1,3-thiazole-4-carbonyl]-(cyclopropylmethyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C1=C(SC(Br)=N1)C=1C=CC(C)=CC=1)CC1CC1 WNPWJUUJTFRWHC-UHFFFAOYSA-N 0.000 claims description 3
- COIWTOBARQHJDJ-UHFFFAOYSA-N n-[2-[[2-bromo-5-(4-methylphenyl)-1,3-thiazole-4-carbonyl]-cyclopropylamino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C1=C(SC(Br)=N1)C=1C=CC(C)=CC=1)C1CC1 COIWTOBARQHJDJ-UHFFFAOYSA-N 0.000 claims description 3
- MJXSPUXGIMQXNY-UHFFFAOYSA-N n-[2-[[2-cyclopropyl-5-(3-methoxyphenyl)-1,3-thiazole-4-carbonyl]-(cyclopropylmethyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(S2)C2CC2)C(=O)N(CCNC(=O)C=2N3C=CSC3=NC=2C)CC2CC2)=C1 MJXSPUXGIMQXNY-UHFFFAOYSA-N 0.000 claims description 3
- XWGNHKOFBAEQCR-UHFFFAOYSA-N n-[2-[[5-(3-cyanophenyl)-2-methyl-1,3-thiazole-4-carbonyl]-(cyclopropylmethyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound C=1C=CC(C#N)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1N2C=CSC2=NC=1C)CC1CC1 XWGNHKOFBAEQCR-UHFFFAOYSA-N 0.000 claims description 3
- QOZIPHCKKGXUTP-UHFFFAOYSA-N n-[2-[[5-(3-cyanophenyl)-2-methyl-1,3-thiazole-4-carbonyl]-cyclopropylamino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound C=1C=CC(C#N)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1N2C=CSC2=NC=1C)C1CC1 QOZIPHCKKGXUTP-UHFFFAOYSA-N 0.000 claims description 3
- HQMILTMYSACADK-UHFFFAOYSA-N n-[2-[[5-(4-chlorophenyl)-2-methyl-1,3-thiazole-4-carbonyl]-(cyclopropylmethyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1N2C=CSC2=NC=1C)CC1CC1 HQMILTMYSACADK-UHFFFAOYSA-N 0.000 claims description 3
- UFTUZAXHMDEMTD-UHFFFAOYSA-N n-[2-[[5-(4-chlorophenyl)-2-methyl-1,3-thiazole-4-carbonyl]-cyclopropylamino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1N2C=CSC2=NC=1C)C1CC1 UFTUZAXHMDEMTD-UHFFFAOYSA-N 0.000 claims description 3
- HCPOHBAGPRTDAP-UHFFFAOYSA-N n-[2-[[5-(4-fluorophenyl)-2-methyl-1,3-thiazole-4-carbonyl]-methylamino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C)C(=O)C=1N=C(C)SC=1C1=CC=C(F)C=C1 HCPOHBAGPRTDAP-UHFFFAOYSA-N 0.000 claims description 3
- WMIREBOPPAUHHO-UHFFFAOYSA-N n-[2-[benzyl-(2-methyl-5-phenyl-1,3-thiazole-4-carbonyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical class C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1N2C=CSC2=NC=1C)CC1=CC=CC=C1 WMIREBOPPAUHHO-UHFFFAOYSA-N 0.000 claims description 3
- GMOJMSVBOAKDDZ-UHFFFAOYSA-N n-[2-[benzyl-[5-(4-fluorophenyl)-2-methyl-1,3-thiazole-4-carbonyl]amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound C=1C=C(F)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1N2C=CSC2=NC=1C)CC1=CC=CC=C1 GMOJMSVBOAKDDZ-UHFFFAOYSA-N 0.000 claims description 3
- WBFKLNTXNLEOKH-UHFFFAOYSA-N n-[2-[cyclohexylmethyl-(2-methyl-5-phenyl-1,3-thiazole-4-carbonyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1N2C=CSC2=NC=1C)CC1CCCCC1 WBFKLNTXNLEOKH-UHFFFAOYSA-N 0.000 claims description 3
- DHJBWWZGKHHBKS-UHFFFAOYSA-N n-[2-[cyclopropyl-(2-cyclopropyl-5-phenyl-1,3-thiazole-4-carbonyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C1=C(SC(=N1)C1CC1)C=1C=CC=CC=1)C1CC1 DHJBWWZGKHHBKS-UHFFFAOYSA-N 0.000 claims description 3
- QYGBTOVUGCTHNV-UHFFFAOYSA-N n-[2-[cyclopropyl-(2-methyl-5-phenyl-1,3-thiazole-4-carbonyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical class C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1N2C=CSC2=NC=1C)C1CC1 QYGBTOVUGCTHNV-UHFFFAOYSA-N 0.000 claims description 3
- LXKMEAMDCCKMCZ-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-(3-methylphenyl)benzoyl]amino]ethyl]-1-benzofuran-4-carboxamide Chemical compound CC1=CC=CC(C=2C(=CC=CC=2)C(=O)N(CCNC(=O)C=2C=3C=COC=3C=CC=2)C2CC2)=C1 LXKMEAMDCCKMCZ-UHFFFAOYSA-N 0.000 claims description 3
- MZBHOKPOECCTRK-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-(3-methylphenyl)benzoyl]amino]ethyl]-1-methylindazole-3-carboxamide Chemical compound CC1=CC=CC(C=2C(=CC=CC=2)C(=O)N(CCNC(=O)C=2C3=CC=CC=C3N(C)N=2)C2CC2)=C1 MZBHOKPOECCTRK-UHFFFAOYSA-N 0.000 claims description 3
- ZFQYWUWXMFNRBD-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-(3-methylphenyl)benzoyl]amino]ethyl]-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound CC1=CC=CC(C=2C(=CC=CC=2)C(=O)N(CCNC(=O)C=2C=3OCCOC=3C=CC=2)C2CC2)=C1 ZFQYWUWXMFNRBD-UHFFFAOYSA-N 0.000 claims description 3
- HFRPWAVUICNEHT-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-(3-methylphenyl)benzoyl]amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C=1C(=CC=CC=1)C=1C=C(C)C=CC=1)C1CC1 HFRPWAVUICNEHT-UHFFFAOYSA-N 0.000 claims description 3
- QHPIIDRLDUDESM-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-(4-fluorophenyl)benzoyl]amino]ethyl]-1-benzofuran-4-carboxamide Chemical compound C1=CC(F)=CC=C1C1=CC=CC=C1C(=O)N(C1CC1)CCNC(=O)C1=CC=CC2=C1C=CO2 QHPIIDRLDUDESM-UHFFFAOYSA-N 0.000 claims description 3
- NMIGXTGPUBZLEA-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-(4-fluorophenyl)benzoyl]amino]ethyl]-1-methylindazole-3-carboxamide Chemical compound C12=CC=CC=C2N(C)N=C1C(=O)NCCN(C(=O)C=1C(=CC=CC=1)C=1C=CC(F)=CC=1)C1CC1 NMIGXTGPUBZLEA-UHFFFAOYSA-N 0.000 claims description 3
- LUKRAHDUHAQQHJ-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-(4-fluorophenyl)benzoyl]amino]ethyl]-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical class C1=CC(F)=CC=C1C1=CC=CC=C1C(=O)N(C1CC1)CCNC(=O)C1=CC=CC2=C1OCCO2 LUKRAHDUHAQQHJ-UHFFFAOYSA-N 0.000 claims description 3
- FVRRONQVEMEWHP-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-(4-fluorophenyl)benzoyl]amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical class CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C=1C(=CC=CC=1)C=1C=CC(F)=CC=1)C1CC1 FVRRONQVEMEWHP-UHFFFAOYSA-N 0.000 claims description 3
- VMSHZKRNYAGXKQ-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-(4-methylphenyl)benzoyl]amino]ethyl]-1-benzofuran-4-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1C(=O)N(C1CC1)CCNC(=O)C1=CC=CC2=C1C=CO2 VMSHZKRNYAGXKQ-UHFFFAOYSA-N 0.000 claims description 3
- KJYOXZSFSWDKGS-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-(4-methylphenyl)benzoyl]amino]ethyl]-1-methylindazole-3-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1C(=O)N(C1CC1)CCNC(=O)C1=NN(C)C2=CC=CC=C12 KJYOXZSFSWDKGS-UHFFFAOYSA-N 0.000 claims description 3
- XDGODKAUCWLMFW-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-(4-methylphenyl)benzoyl]amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C=1C(=CC=CC=1)C=1C=CC(C)=CC=1)C1CC1 XDGODKAUCWLMFW-UHFFFAOYSA-N 0.000 claims description 3
- DAMBOVRYUQZFHO-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-cyclopropyl-5-(3-methoxyphenyl)-1,3-thiazole-4-carbonyl]amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(S2)C2CC2)C(=O)N(CCNC(=O)C=2N3C=CSC3=NC=2C)C2CC2)=C1 DAMBOVRYUQZFHO-UHFFFAOYSA-N 0.000 claims description 3
- QIHIWJJQNJNMFD-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-cyclopropyl-5-(3-methylphenyl)-1,3-thiazole-4-carbonyl]amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C1=C(SC(=N1)C1CC1)C=1C=C(C)C=CC=1)C1CC1 QIHIWJJQNJNMFD-UHFFFAOYSA-N 0.000 claims description 3
- ICEHRAAVXPPHSZ-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-methyl-5-(4-methylphenyl)-1,3-thiazole-4-carbonyl]amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound C=1C=C(C)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1N2C=CSC2=NC=1C)C1CC1 ICEHRAAVXPPHSZ-UHFFFAOYSA-N 0.000 claims description 3
- GIWPFCBEXRLBHY-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-methyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazole-4-carbonyl]amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1N2C=CSC2=NC=1C)C1CC1 GIWPFCBEXRLBHY-UHFFFAOYSA-N 0.000 claims description 3
- KCHXFYFNGHXAOX-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-methyl-5-[4-(trifluoromethyl)phenyl]-1,3-thiazole-4-carbonyl]amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1N2C=CSC2=NC=1C)C1CC1 KCHXFYFNGHXAOX-UHFFFAOYSA-N 0.000 claims description 3
- FRJHZAQDOHSYDM-UHFFFAOYSA-N n-[2-[cyclopropyl-[5-(3,4-dimethylphenyl)-2-methyl-1,3-thiazole-4-carbonyl]amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound C=1C=C(C)C(C)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1N2C=CSC2=NC=1C)C1CC1 FRJHZAQDOHSYDM-UHFFFAOYSA-N 0.000 claims description 3
- VNKRYGJWCFWAQX-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-(2-cyclopropyl-5-phenyl-1,3-thiazole-4-carbonyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C1=C(SC(=N1)C1CC1)C=1C=CC=CC=1)CC1CC1 VNKRYGJWCFWAQX-UHFFFAOYSA-N 0.000 claims description 3
- WYOZDFIZFHWBKQ-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-(2-methyl-5-phenyl-1,3-thiazole-4-carbonyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1N2C=CSC2=NC=1C)CC1CC1 WYOZDFIZFHWBKQ-UHFFFAOYSA-N 0.000 claims description 3
- AFEUDEPKKPWLPJ-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-[2-(3-methylphenyl)benzoyl]amino]ethyl]-1-benzofuran-4-carboxamide Chemical compound CC1=CC=CC(C=2C(=CC=CC=2)C(=O)N(CCNC(=O)C=2C=3C=COC=3C=CC=2)CC2CC2)=C1 AFEUDEPKKPWLPJ-UHFFFAOYSA-N 0.000 claims description 3
- NURIUAQPKGMHMK-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-[2-(3-methylphenyl)benzoyl]amino]ethyl]-1-methylindazole-3-carboxamide Chemical compound CC1=CC=CC(C=2C(=CC=CC=2)C(=O)N(CCNC(=O)C=2C3=CC=CC=C3N(C)N=2)CC2CC2)=C1 NURIUAQPKGMHMK-UHFFFAOYSA-N 0.000 claims description 3
- VJVFELSTTPRFII-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-[2-(3-methylphenyl)benzoyl]amino]ethyl]-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical class CC1=CC=CC(C=2C(=CC=CC=2)C(=O)N(CCNC(=O)C=2C=3OCCOC=3C=CC=2)CC2CC2)=C1 VJVFELSTTPRFII-UHFFFAOYSA-N 0.000 claims description 3
- YAMPZSZYTJPQFF-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-[2-(3-methylphenyl)benzoyl]amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical class CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C=1C(=CC=CC=1)C=1C=C(C)C=CC=1)CC1CC1 YAMPZSZYTJPQFF-UHFFFAOYSA-N 0.000 claims description 3
- KNBOJLAYSNCYRZ-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-[2-(4-fluorophenyl)benzoyl]amino]ethyl]-1-benzofuran-4-carboxamide Chemical compound C1=CC(F)=CC=C1C1=CC=CC=C1C(=O)N(CC1CC1)CCNC(=O)C1=CC=CC2=C1C=CO2 KNBOJLAYSNCYRZ-UHFFFAOYSA-N 0.000 claims description 3
- CQHCSHOXFYCHBU-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-[2-(4-fluorophenyl)benzoyl]amino]ethyl]-1-methylindazole-3-carboxamide Chemical compound C12=CC=CC=C2N(C)N=C1C(=O)NCCN(C(=O)C=1C(=CC=CC=1)C=1C=CC(F)=CC=1)CC1CC1 CQHCSHOXFYCHBU-UHFFFAOYSA-N 0.000 claims description 3
- IYZIXWPHEOZNIX-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-[2-(4-fluorophenyl)benzoyl]amino]ethyl]-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical class C1=CC(F)=CC=C1C1=CC=CC=C1C(=O)N(CC1CC1)CCNC(=O)C1=CC=CC2=C1OCCO2 IYZIXWPHEOZNIX-UHFFFAOYSA-N 0.000 claims description 3
- WIBUOKAPNVQSCW-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-[2-(4-methylphenyl)benzoyl]amino]ethyl]-1-benzofuran-4-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1C(=O)N(CC1CC1)CCNC(=O)C1=CC=CC2=C1C=CO2 WIBUOKAPNVQSCW-UHFFFAOYSA-N 0.000 claims description 3
- OFNLXGCVNFBNHX-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-[2-(4-methylphenyl)benzoyl]amino]ethyl]-1-methylindazole-3-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1C(=O)N(CC1CC1)CCNC(=O)C1=NN(C)C2=CC=CC=C12 OFNLXGCVNFBNHX-UHFFFAOYSA-N 0.000 claims description 3
- XOCNCMKTCVINRW-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-[2-(4-methylphenyl)benzoyl]amino]ethyl]-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical class C1=CC(C)=CC=C1C1=CC=CC=C1C(=O)N(CC1CC1)CCNC(=O)C1=CC=CC2=C1OCCO2 XOCNCMKTCVINRW-UHFFFAOYSA-N 0.000 claims description 3
- IUVZRVLURBWBQA-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-[2-(4-methylphenyl)benzoyl]amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical class CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C=1C(=CC=CC=1)C=1C=CC(C)=CC=1)CC1CC1 IUVZRVLURBWBQA-UHFFFAOYSA-N 0.000 claims description 3
- NADANFJHESYCQI-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-[2-cyclopropyl-5-(3-methylphenyl)-1,3-thiazole-4-carbonyl]amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCCN(C(=O)C1=C(SC(=N1)C1CC1)C=1C=C(C)C=CC=1)CC1CC1 NADANFJHESYCQI-UHFFFAOYSA-N 0.000 claims description 3
- VAICSNGLLGRSRX-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-[2-methyl-5-(4-methylphenyl)-1,3-thiazole-4-carbonyl]amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound C=1C=C(C)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1N2C=CSC2=NC=1C)CC1CC1 VAICSNGLLGRSRX-UHFFFAOYSA-N 0.000 claims description 3
- BDGJLNNBWWHJOU-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-[2-methyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazole-4-carbonyl]amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1N2C=CSC2=NC=1C)CC1CC1 BDGJLNNBWWHJOU-UHFFFAOYSA-N 0.000 claims description 3
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160077216A (ko) * | 2013-11-19 | 2016-07-01 | 액테리온 파마슈티칼 리미티드 | 트리시클릭 피페리딘 화합물 |
| KR20170044204A (ko) * | 2014-09-03 | 2017-04-24 | 씨4엑스 디스커버리 리미티드 | 오렉신―1 수용체의 억제제로서의 치료 화합물 |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8084601B2 (en) | 2008-09-11 | 2011-12-27 | Royal Holloway And Bedford New College Royal Holloway, University Of London | Oligomers |
| WO2010044054A1 (en) * | 2008-10-14 | 2010-04-22 | Actelion Pharmaceuticals Ltd | Phenethylamide derivatives and their heterocyclic analogues |
| US8680275B2 (en) | 2009-10-23 | 2014-03-25 | Janssen Pharmaceutica Nv | Fused heterocyclic compounds as orexin receptor modulators |
| KR101859409B1 (ko) | 2009-10-23 | 2018-05-18 | 얀센 파마슈티카 엔.브이. | 오렉신 수용체 조절제로서의 이치환된 옥타하이드로피롤로[3,4-c]피롤 |
| US9062044B2 (en) | 2009-10-23 | 2015-06-23 | Janssen Pharmaceutica Nv | Disubstituted octahydropyrrolo[3,4-c]pyrroles as orexin receptor modulators |
| WO2011073316A1 (en) * | 2009-12-18 | 2011-06-23 | Novartis Ag | 4-aryl-butane-1,3-diamides |
| JP5847830B2 (ja) * | 2010-11-10 | 2016-01-27 | アクテリオン ファーマシューティカルズ リミテッドActelion Pharmaceuticals Ltd | オレキシン受容体拮抗薬として有用なラクタム誘導体 |
| US9586962B2 (en) | 2011-04-20 | 2017-03-07 | Janssen Pharmaceutica Nv | Disubstituted octahydropyrrolo [3,4-C] pyrroles as orexin receptor modulators |
| US9440982B2 (en) | 2012-02-07 | 2016-09-13 | Eolas Therapeutics, Inc. | Substituted prolines/piperidines as orexin receptor antagonists |
| NZ628491A (en) | 2012-02-07 | 2016-06-24 | Eolas Therapeutics Inc | Substituted prolines / piperidines as orexin receptor antagonists |
| JP6663909B2 (ja) | 2014-08-13 | 2020-03-13 | エオラス セラピューティクス, インコーポレイテッド | オレキシンレセプターモジュレーターとしてのジフルオロピロリジン |
| GB201601703D0 (en) | 2016-01-29 | 2016-03-16 | C4X Discovery Ltd | Therapeutic compounds |
| SI3414241T1 (sl) | 2016-02-12 | 2022-10-28 | Astrazeneca Ab | Halo-substituitani piperidini kot modulatorji receptorja oreksina |
| PT3426251T (pt) | 2016-03-10 | 2022-07-27 | Janssen Pharmaceutica Nv | Métodos de tratamento da depressão utilizando antagonistas dos recetores de orexina-2 |
| US20190151304A1 (en) | 2016-05-10 | 2019-05-23 | Inserm (Institut National De La Santé Et De La Rechercjae Médicale | Methods and pharmaceutical compositions for the treatment of autoimmune inflammatory |
| GB201702174D0 (en) | 2017-02-09 | 2017-03-29 | Benevolentai Bio Ltd | Orexin receptor antagonists |
| GB201707504D0 (en) | 2017-05-10 | 2017-06-21 | Benevolentai Bio Ltd | Orexin receptor antagonists |
| GB201707499D0 (en) | 2017-05-10 | 2017-06-21 | Benevolentai Bio Ltd | Orexin receptor antagonists |
| WO2025224168A1 (en) | 2024-04-24 | 2025-10-30 | Idorsia Pharmaceuticals Ltd | Aryl sulfone and sulfanone derivatives as orexin receptor modulators |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2381995A (en) | 1994-04-29 | 1995-11-29 | Pharmacia & Upjohn Company | Methanol derivatives for treatment of retroviral infections especially hiv infections |
| AU2001272476A1 (en) * | 2000-06-16 | 2001-12-24 | Smithkline Beecham Plc | Piperidines for use as orexin receptor antagonists |
| JP4028711B2 (ja) * | 2001-10-31 | 2007-12-26 | 株式会社アーレスティ | 金型冷却装置 |
| GB0130341D0 (en) | 2001-12-19 | 2002-02-06 | Smithkline Beecham Plc | Compounds |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160077216A (ko) * | 2013-11-19 | 2016-07-01 | 액테리온 파마슈티칼 리미티드 | 트리시클릭 피페리딘 화합물 |
| KR20170044204A (ko) * | 2014-09-03 | 2017-04-24 | 씨4엑스 디스커버리 리미티드 | 오렉신―1 수용체의 억제제로서의 치료 화합물 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101778846B (zh) | 2012-11-14 |
| US20110263662A1 (en) | 2011-10-27 |
| EP2188282B1 (en) | 2013-01-23 |
| CN101778846A (zh) | 2010-07-14 |
| RU2010109455A (ru) | 2011-09-20 |
| CA2694993A1 (en) | 2009-02-19 |
| WO2009022311A2 (en) | 2009-02-19 |
| BRPI0815079A2 (pt) | 2015-02-03 |
| ES2400830T3 (es) | 2013-04-12 |
| MX2010001575A (es) | 2010-03-15 |
| JP2010536740A (ja) | 2010-12-02 |
| AU2008288151A1 (en) | 2009-02-19 |
| EP2188282A2 (en) | 2010-05-26 |
| WO2009022311A3 (en) | 2009-04-09 |
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