JP2010536740A5 - - Google Patents
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- JP2010536740A5 JP2010536740A5 JP2010520669A JP2010520669A JP2010536740A5 JP 2010536740 A5 JP2010536740 A5 JP 2010536740A5 JP 2010520669 A JP2010520669 A JP 2010520669A JP 2010520669 A JP2010520669 A JP 2010520669A JP 2010536740 A5 JP2010536740 A5 JP 2010536740A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- thiazole
- amino
- carbonyl
- amide
- 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.)
- Ceased
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- -1 bromo, cyclopropyl Chemical group 0.000 claims 64
- 150000001408 amides Chemical class 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 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 14
- 125000001424 substituent group Chemical group 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- OVVDFORZEGKEJM-UHFFFAOYSA-N 1-methylindazole-3-carboxylic acid Chemical compound C1=CC=C2N(C)N=C(C(O)=O)C2=C1 OVVDFORZEGKEJM-UHFFFAOYSA-N 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- YFOICSSNYXWWBW-UHFFFAOYSA-N 2-methyl-5-(4-methylphenyl)-1,3-thiazole-4-carboxylic acid Chemical compound S1C(C)=NC(C(O)=O)=C1C1=CC=C(C)C=C1 YFOICSSNYXWWBW-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004565 2,3-dihydrobenzofuran-4-yl group Chemical group O1CCC2=C1C=CC=C2* 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- TVCAGLYHSWKSRJ-UHFFFAOYSA-N 2-amino-n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-(cyclopropylmethyl)-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)CC1CC1 TVCAGLYHSWKSRJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- MHXCJKPVJHFYJV-UHFFFAOYSA-N 2-amino-n-cyclopropyl-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)C1CC1 MHXCJKPVJHFYJV-UHFFFAOYSA-N 0.000 claims 1
- WGMIKMPNFFBWSC-UHFFFAOYSA-N 2-amino-n-cyclopropyl-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)C2CC2)=C1 WGMIKMPNFFBWSC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- USFTXTZEFRYRFR-UHFFFAOYSA-N 2-amino-n-cyclopropyl-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-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=2OCCOC=2C=CC=1)C1CC1 USFTXTZEFRYRFR-UHFFFAOYSA-N 0.000 claims 1
- CSEWYJMWIQZIJJ-UHFFFAOYSA-N 2-amino-n-cyclopropyl-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)C1CC1 CSEWYJMWIQZIJJ-UHFFFAOYSA-N 0.000 claims 1
- BTUWDRMXZYAQGY-UHFFFAOYSA-N 2-amino-n-cyclopropyl-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)C2CC2)=C1 BTUWDRMXZYAQGY-UHFFFAOYSA-N 0.000 claims 1
- QZQPJXVUEYNOLW-UHFFFAOYSA-N 2-amino-n-cyclopropyl-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)C1CC1 QZQPJXVUEYNOLW-UHFFFAOYSA-N 0.000 claims 1
- HKYBFLVBMUJZPV-UHFFFAOYSA-N 2-bromo-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(Br)S2)C(=O)N(CCNC(=O)C=2C3=CC=CC=C3N(C)N=2)CC2CC2)=C1 HKYBFLVBMUJZPV-UHFFFAOYSA-N 0.000 claims 1
- RKWWULYALIHFJG-UHFFFAOYSA-N 2-bromo-n-(cyclopropylmethyl)-n-[2-[(1-methylindazole-3-carbonyl)amino]ethyl]-5-(4-methylphenyl)-1,3-thiazole-4-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(C(=O)N(CCNC(=O)C=2C3=CC=CC=C3N(C)N=2)CC2CC2)N=C(Br)S1 RKWWULYALIHFJG-UHFFFAOYSA-N 0.000 claims 1
- CYWZXFJKTQZINY-UHFFFAOYSA-N 2-bromo-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(Br)S2)C(=O)N(CCNC(=O)C=2C3=CC=CC=C3N(C)N=2)C2CC2)=C1 CYWZXFJKTQZINY-UHFFFAOYSA-N 0.000 claims 1
- SJJHLXXNJWTTFY-UHFFFAOYSA-N 2-bromo-n-cyclopropyl-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(Br)S2)C(=O)N(CCNC(=O)C=2C=3OCCOC=3C=CC=2)C2CC2)=C1 SJJHLXXNJWTTFY-UHFFFAOYSA-N 0.000 claims 1
- OQXCNTVFUGFAKJ-UHFFFAOYSA-N 2-bromo-n-cyclopropyl-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)C2CC2)N=C(Br)S1 OQXCNTVFUGFAKJ-UHFFFAOYSA-N 0.000 claims 1
- SXCQUJBYUQEUEE-UHFFFAOYSA-N 2-bromo-n-cyclopropyl-n-[2-[(1-methylindazole-3-carbonyl)amino]ethyl]-5-(4-methylphenyl)-1,3-thiazole-4-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(C(=O)N(CCNC(=O)C=2C3=CC=CC=C3N(C)N=2)C2CC2)N=C(Br)S1 SXCQUJBYUQEUEE-UHFFFAOYSA-N 0.000 claims 1
- IKIDLUICQHHWKP-UHFFFAOYSA-N 2-cyclopropyl-5-(3-methylphenyl)-1,3-thiazole-4-carboxylic acid Chemical compound CC1=CC=CC(C2=C(N=C(S2)C2CC2)C(O)=O)=C1 IKIDLUICQHHWKP-UHFFFAOYSA-N 0.000 claims 1
- DETNRAFQTNXTAW-UHFFFAOYSA-N 2-cyclopropyl-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(S2)C2CC2)C(=O)N(CCNC(=O)C=2C3=CC=CC=C3N(C)N=2)CC2CC2)=C1 DETNRAFQTNXTAW-UHFFFAOYSA-N 0.000 claims 1
- IEPBGVWKZFSEFU-UHFFFAOYSA-N 2-cyclopropyl-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=2OCCOC=2C=1C(=O)NCCN(C(=O)C1=C(SC(=N1)C1CC1)C=1C=CC=CC=1)CC1CC1 IEPBGVWKZFSEFU-UHFFFAOYSA-N 0.000 claims 1
- WLXBSLQRQDSSKW-UHFFFAOYSA-N 2-cyclopropyl-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(S2)C2CC2)C(=O)N(CCNC(=O)C=2C3=CC=CC=C3N(C)N=2)CC2CC2)=C1 WLXBSLQRQDSSKW-UHFFFAOYSA-N 0.000 claims 1
- TVRXIHYDFVZLRG-UHFFFAOYSA-N 2-cyclopropyl-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(=N1)C1CC1)C=1C=CC=CC=1)CC1CC1 TVRXIHYDFVZLRG-UHFFFAOYSA-N 0.000 claims 1
- YTGZVADHWFMCNP-UHFFFAOYSA-N 5-(3-cyanophenyl)-n-(cyclopropylmethyl)-2-methyl-n-[2-[(1-methylindazole-3-carbonyl)amino]ethyl]-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC(C#N)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C2=CC=CC=C2N(C)N=1)CC1CC1 YTGZVADHWFMCNP-UHFFFAOYSA-N 0.000 claims 1
- QCQUMOJSPKIXGE-UHFFFAOYSA-N 5-(3-cyanophenyl)-n-(cyclopropylmethyl)-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-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=2OCCOC=2C=CC=1)CC1CC1 QCQUMOJSPKIXGE-UHFFFAOYSA-N 0.000 claims 1
- ONQHPEZCPKDZRV-UHFFFAOYSA-N 5-(3-cyanophenyl)-n-cyclopropyl-2-methyl-n-[2-[(1-methylindazole-3-carbonyl)amino]ethyl]-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC(C#N)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C2=CC=CC=C2N(C)N=1)C1CC1 ONQHPEZCPKDZRV-UHFFFAOYSA-N 0.000 claims 1
- HHXKNGRNDSGMLG-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-methyl-1,3-thiazole-4-carboxylic acid Chemical compound S1C(C)=NC(C(O)=O)=C1C1=CC=C(Cl)C=C1 HHXKNGRNDSGMLG-UHFFFAOYSA-N 0.000 claims 1
- LUODIVPWTSGZAP-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(cyclopropylmethyl)-2-methyl-n-[2-[(1-methylindazole-3-carbonyl)amino]ethyl]-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C2=CC=CC=C2N(C)N=1)CC1CC1 LUODIVPWTSGZAP-UHFFFAOYSA-N 0.000 claims 1
- AXNSQAGXSNUTHT-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-cyclopropyl-2-methyl-n-[2-[(1-methylindazole-3-carbonyl)amino]ethyl]-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C2=CC=CC=C2N(C)N=1)C1CC1 AXNSQAGXSNUTHT-UHFFFAOYSA-N 0.000 claims 1
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- KMLGNWLYDRDUKP-UHFFFAOYSA-N n-[1-(1-benzofuran-4-carbonylamino)-3-phenylpropan-2-yl]-n-benzyl-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(C(CNC(=O)C=1C=2C=COC=2C=CC=1)CC=1C=CC=CC=1)CC1=CC=CC=C1 KMLGNWLYDRDUKP-UHFFFAOYSA-N 0.000 claims 1
- QARPMDZQRPJBEC-UHFFFAOYSA-N n-[1-(1-benzofuran-4-carbonylamino)-4-methylpentan-2-yl]-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCC(CC(C)C)NC(=O)C=1N=C(C)SC=1C1=CC=CC=C1 QARPMDZQRPJBEC-UHFFFAOYSA-N 0.000 claims 1
- OTUMXLMAHZREQK-UHFFFAOYSA-N n-[1-(1-benzofuran-4-carbonylamino)-4-methylpentan-2-yl]-n,2-dimethyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCC(CC(C)C)N(C)C(=O)C=1N=C(C)SC=1C1=CC=CC=C1 OTUMXLMAHZREQK-UHFFFAOYSA-N 0.000 claims 1
- LHTHZMWOQDGTND-UHFFFAOYSA-N n-[1-(1-benzofuran-4-carbonylamino)-4-methylpentan-2-yl]-n-benzyl-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCC(CC(C)C)N(C(=O)C1=C(SC(C)=N1)C=1C=CC=CC=1)CC1=CC=CC=C1 LHTHZMWOQDGTND-UHFFFAOYSA-N 0.000 claims 1
- KVUKIKWBGPQYEU-UHFFFAOYSA-N n-[1-(1-benzofuran-4-carbonylamino)-4-phenylbutan-2-yl]-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)NC(CNC(=O)C=1C=2C=COC=2C=CC=1)CCC1=CC=CC=C1 KVUKIKWBGPQYEU-UHFFFAOYSA-N 0.000 claims 1
- PWEJURCTDWVVGA-UHFFFAOYSA-N n-[1-(1-benzofuran-4-carbonylamino)-4-phenylbutan-2-yl]-n,2-dimethyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound N1=C(C)SC(C=2C=CC=CC=2)=C1C(=O)N(C)C(CNC(=O)C=1C=2C=COC=2C=CC=1)CCC1=CC=CC=C1 PWEJURCTDWVVGA-UHFFFAOYSA-N 0.000 claims 1
- ZFWHXRYEEMYVIV-UHFFFAOYSA-N n-[1-(1-benzofuran-4-carbonylamino)-4-phenylbutan-2-yl]-n-benzyl-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(C(CCC=1C=CC=CC=1)CNC(=O)C=1C=2C=COC=2C=CC=1)CC1=CC=CC=C1 ZFWHXRYEEMYVIV-UHFFFAOYSA-N 0.000 claims 1
- DPYQTKLUMRYXAH-UHFFFAOYSA-N n-[1-(1-benzofuran-4-carbonylamino)propan-2-yl]-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCC(C)NC(=O)C=1N=C(C)SC=1C1=CC=CC=C1 DPYQTKLUMRYXAH-UHFFFAOYSA-N 0.000 claims 1
- MCLBRDBRCQWTJP-UHFFFAOYSA-N n-[1-(1-benzofuran-4-carbonylamino)propan-2-yl]-n,2-dimethyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCC(C)N(C)C(=O)C=1N=C(C)SC=1C1=CC=CC=C1 MCLBRDBRCQWTJP-UHFFFAOYSA-N 0.000 claims 1
- KJAKYOZCMFXQIM-UHFFFAOYSA-N n-[1-(1-benzofuran-4-carbonylamino)propan-2-yl]-n-benzyl-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCC(C)N(C(=O)C1=C(SC(C)=N1)C=1C=CC=CC=1)CC1=CC=CC=C1 KJAKYOZCMFXQIM-UHFFFAOYSA-N 0.000 claims 1
- CMIJOZZEYALWLU-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)-1-cyclopropylethyl]-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)NC(CNC(=O)C=1C=2C=COC=2C=CC=1)C1CC1 CMIJOZZEYALWLU-UHFFFAOYSA-N 0.000 claims 1
- BFFFDINOGVIUIJ-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)-1-cyclopropylethyl]-n,2-dimethyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound N1=C(C)SC(C=2C=CC=CC=2)=C1C(=O)N(C)C(CNC(=O)C=1C=2C=COC=2C=CC=1)C1CC1 BFFFDINOGVIUIJ-UHFFFAOYSA-N 0.000 claims 1
- VQYKPJANGCCNTG-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)-1-cyclopropylethyl]-n-benzyl-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(C(CNC(=O)C=1C=2C=COC=2C=CC=1)C1CC1)CC1=CC=CC=C1 VQYKPJANGCCNTG-UHFFFAOYSA-N 0.000 claims 1
- RWWVHFOYBPSYBO-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-2-bromo-n-(cyclopropylmethyl)-5-(3-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(Br)S2)C(=O)N(CCNC(=O)C=2C=3C=COC=3C=CC=2)CC2CC2)=C1 RWWVHFOYBPSYBO-UHFFFAOYSA-N 0.000 claims 1
- ICXIXFPRNQSPJT-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-2-bromo-n-(cyclopropylmethyl)-5-(4-methylphenyl)-1,3-thiazole-4-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(C(=O)N(CCNC(=O)C=2C=3C=COC=3C=CC=2)CC2CC2)N=C(Br)S1 ICXIXFPRNQSPJT-UHFFFAOYSA-N 0.000 claims 1
- DSCYCHFSAXBKQA-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-2-bromo-n-cyclopropyl-5-(3-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(Br)S2)C(=O)N(CCNC(=O)C=2C=3C=COC=3C=CC=2)C2CC2)=C1 DSCYCHFSAXBKQA-UHFFFAOYSA-N 0.000 claims 1
- KWEQOTFEPDWKIM-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-2-bromo-n-cyclopropyl-5-(4-methylphenyl)-1,3-thiazole-4-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(C(=O)N(CCNC(=O)C=2C=3C=COC=3C=CC=2)C2CC2)N=C(Br)S1 KWEQOTFEPDWKIM-UHFFFAOYSA-N 0.000 claims 1
- LAOJEDZIJBBVHO-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-2-cyclopropyl-n-(cyclopropylmethyl)-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)CC2CC2)=C1 LAOJEDZIJBBVHO-UHFFFAOYSA-N 0.000 claims 1
- ZBGURWWSIVPAKC-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-2-cyclopropyl-n-(cyclopropylmethyl)-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)CC2CC2)=C1 ZBGURWWSIVPAKC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- RIRVPTSLMNUFJX-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-cyclopropyl-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)C1CC1 RIRVPTSLMNUFJX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- ILURMEHRPYFDFH-UHFFFAOYSA-N n-[2-(2,3-dihydro-1,4-benzodioxine-5-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=2OCCOC=2C=CC=1)CCC1=CC=CC=C1 ILURMEHRPYFDFH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 compound 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 compound 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 1
- GJFSYVCZQFTEQU-UHFFFAOYSA-N n-[2-[(2-phenylbenzoyl)amino]propyl]-1-benzofuran-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCC(C)NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GJFSYVCZQFTEQU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- SIFSMYIHLBXGDJ-UHFFFAOYSA-N n-[2-[3,3-dimethylbutyl-(2-methyl-5-phenyl-1,3-thiazole-4-carbonyl)amino]ethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound S1C(C)=NC(C(=O)N(CCNC(=O)C=2N3C=CSC3=NC=2C)CCC(C)(C)C)=C1C1=CC=CC=C1 SIFSMYIHLBXGDJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 compound 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 1
- BSTNLAVHVXBKQK-UHFFFAOYSA-N n-[2-[benzyl-(2-methyl-5-phenyl-1,3-thiazole-4-carbonyl)amino]propyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCC(C)N(C(=O)C1=C(SC(C)=N1)C=1C=CC=CC=1)CC1=CC=CC=C1 BSTNLAVHVXBKQK-UHFFFAOYSA-N 0.000 claims 1
- GAVXZCWCKNXSMU-UHFFFAOYSA-N n-[2-[benzyl-(2-phenylbenzoyl)amino]-2-cyclopropylethyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCC(N(CC=1C=CC=CC=1)C(=O)C=1C(=CC=CC=1)C=1C=CC=CC=1)C1CC1 GAVXZCWCKNXSMU-UHFFFAOYSA-N 0.000 claims 1
- FGYRHKNXWQDYDK-UHFFFAOYSA-N n-[2-[benzyl-(2-phenylbenzoyl)amino]-3-methylbutyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCC(C(C)C)N(C(=O)C=1C(=CC=CC=1)C=1C=CC=CC=1)CC1=CC=CC=C1 FGYRHKNXWQDYDK-UHFFFAOYSA-N 0.000 claims 1
- YJCYQYNSSHZNHU-UHFFFAOYSA-N n-[2-[benzyl-(2-phenylbenzoyl)amino]-3-phenylpropyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCC(N(CC=1C=CC=CC=1)C(=O)C=1C(=CC=CC=1)C=1C=CC=CC=1)CC1=CC=CC=C1 YJCYQYNSSHZNHU-UHFFFAOYSA-N 0.000 claims 1
- QIJHAKBJQRKDIO-UHFFFAOYSA-N n-[2-[benzyl-(2-phenylbenzoyl)amino]-4-methylpentyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCC(CC(C)C)N(C(=O)C=1C(=CC=CC=1)C=1C=CC=CC=1)CC1=CC=CC=C1 QIJHAKBJQRKDIO-UHFFFAOYSA-N 0.000 claims 1
- BOVNVVARRWJJAD-UHFFFAOYSA-N n-[2-[benzyl-(2-phenylbenzoyl)amino]-4-phenylbutyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCC(N(CC=1C=CC=CC=1)C(=O)C=1C(=CC=CC=1)C=1C=CC=CC=1)CCC1=CC=CC=C1 BOVNVVARRWJJAD-UHFFFAOYSA-N 0.000 claims 1
- UHQBPGZXKKJNKH-UHFFFAOYSA-N n-[2-[benzyl-(2-phenylbenzoyl)amino]propyl]-6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound CC=1N=C2SC=CN2C=1C(=O)NCC(C)N(C(=O)C=1C(=CC=CC=1)C=1C=CC=CC=1)CC1=CC=CC=C1 UHQBPGZXKKJNKH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 compound 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- LUKRAHDUHAQQHJ-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-(4-fluorophenyl)benzoyl]amino]ethyl]-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound C1=CC(F)=CC=C1C1=CC=CC=C1C(=O)N(C1CC1)CCNC(=O)C1=CC=CC2=C1OCCO2 LUKRAHDUHAQQHJ-UHFFFAOYSA-N 0.000 claims 1
- FVRRONQVEMEWHP-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-(4-fluorophenyl)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(F)=CC=1)C1CC1 FVRRONQVEMEWHP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- KMNHEMHGQJGOAN-UHFFFAOYSA-N n-[2-[cyclopropyl-[2-(4-methylphenyl)benzoyl]amino]ethyl]-2,3-dihydro-1,4-benzodioxine-5-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1C(=O)N(C1CC1)CCNC(=O)C1=CC=CC2=C1OCCO2 KMNHEMHGQJGOAN-UHFFFAOYSA-N 0.000 claims 1
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Applications Claiming Priority (2)
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| PCT/IB2008/053264 WO2009022311A2 (en) | 2007-08-15 | 2008-08-14 | 1,2-diamido-ethylene derivatives as orexin antagonists |
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| JP2010536740A JP2010536740A (ja) | 2010-12-02 |
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| EP (1) | EP2188282B1 (Direct) |
| JP (1) | JP2010536740A (Direct) |
| KR (1) | KR20100055464A (Direct) |
| CN (1) | CN101778846B (Direct) |
| AU (1) | AU2008288151A1 (Direct) |
| BR (1) | BRPI0815079A2 (Direct) |
| CA (1) | CA2694993A1 (Direct) |
| ES (1) | ES2400830T3 (Direct) |
| MX (1) | MX2010001575A (Direct) |
| RU (1) | RU2010109455A (Direct) |
| WO (1) | WO2009022311A2 (Direct) |
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| US8084601B2 (en) | 2008-09-11 | 2011-12-27 | Royal Holloway And Bedford New College Royal Holloway, University Of London | Oligomers |
| CA2739344A1 (en) * | 2008-10-14 | 2010-04-22 | Actelion Pharmaceuticals Ltd | Phenethylamide derivatives and their heterocyclic analogues |
| WO2011050202A1 (en) | 2009-10-23 | 2011-04-28 | Janssen Pharmaceutica Nv | Fused heterocyclic compounds as orexin receptor modulators |
| JP5847087B2 (ja) | 2009-10-23 | 2016-01-20 | ヤンセン ファーマシューティカ エヌ．ベー． | オレキシン受容体調節因子としての縮合複素環式化合物 |
| HUE043962T2 (hu) | 2009-10-23 | 2019-09-30 | Janssen Pharmaceutica Nv | Diszubsztituált oktahidro-pirrolo[3,4-C]pirrolok mint orexin receptor modulátorok |
| WO2011073316A1 (en) * | 2009-12-18 | 2011-06-23 | Novartis Ag | 4-aryl-butane-1,3-diamides |
| US9242970B2 (en) * | 2010-11-10 | 2016-01-26 | Actelion Pharmaceuticals Ltd. | Lactam derivatives useful as orexin receptor antagonists |
| WO2012145581A1 (en) | 2011-04-20 | 2012-10-26 | Janssen Pharmaceutica Nv | Disubstituted octahy-dropyrrolo [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 |
| RU2014136339A (ru) | 2012-02-07 | 2016-03-27 | Иолас Терапьютикс, Инк. | Замещенные пролины/пиперидины как антагонисты орексиновых рецепторов |
| AR098436A1 (es) * | 2013-11-19 | 2016-05-26 | Actelion Pharmaceuticals Ltd | Compuestos tricíclicos de piperidina |
| TW201613902A (en) | 2014-08-13 | 2016-04-16 | Eolas Therapeutics Inc | Difluoropyrrolidines as orexin receptor modulators |
| GB201415569D0 (en) * | 2014-09-03 | 2014-10-15 | C4X Discovery Ltd | Therapeutic Compounds |
| GB201601703D0 (en) | 2016-01-29 | 2016-03-16 | C4X Discovery Ltd | Therapeutic compounds |
| CN109219606B (zh) | 2016-02-12 | 2021-10-01 | 阿斯利康(瑞典)有限公司 | 食欲素受体调节剂的卤素取代的哌啶 |
| CA3016706A1 (en) | 2016-03-10 | 2017-09-14 | Janssen Pharmaceutica Nv | Methods of treating depression using orexin-2 receptor antagonists |
| 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 |
| JP4611608B2 (ja) * | 2000-06-16 | 2011-01-12 | スミスクライン ビーチャム ピー エル シー | オレキシン受容体アンタゴニストとして使用するためのピペリジン |
| 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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- 2008-08-14 US US12/673,382 patent/US20110263662A1/en not_active Abandoned
- 2008-08-14 CA CA2694993A patent/CA2694993A1/en not_active Abandoned
- 2008-08-14 JP JP2010520669A patent/JP2010536740A/ja not_active Ceased
- 2008-08-14 EP EP08807317A patent/EP2188282B1/en not_active Not-in-force
- 2008-08-14 WO PCT/IB2008/053264 patent/WO2009022311A2/en not_active Ceased
- 2008-08-14 CN CN2008801035335A patent/CN101778846B/zh not_active Expired - Fee Related
- 2008-08-14 AU AU2008288151A patent/AU2008288151A1/en not_active Abandoned
- 2008-08-14 ES ES08807317T patent/ES2400830T3/es active Active
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