JP2010520195A5 - - Google Patents
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- Publication number
- JP2010520195A5 JP2010520195A5 JP2009551312A JP2009551312A JP2010520195A5 JP 2010520195 A5 JP2010520195 A5 JP 2010520195A5 JP 2009551312 A JP2009551312 A JP 2009551312A JP 2009551312 A JP2009551312 A JP 2009551312A JP 2010520195 A5 JP2010520195 A5 JP 2010520195A5
- Authority
- JP
- Japan
- Prior art keywords
- thiazol
- methyl
- phenoxy
- propionamide
- difluoro
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 23
- 239000000651 prodrug Substances 0.000 claims 16
- 229940002612 prodrug Drugs 0.000 claims 16
- 239000012453 solvate Substances 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 125000003342 alkenyl group Chemical group 0.000 claims 12
- 125000000304 alkynyl group Chemical group 0.000 claims 12
- -1 arylallyl Chemical group 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
- 125000004043 oxo group Chemical group O=* 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 10
- 239000012190 activator Substances 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 238000000034 method Methods 0.000 claims 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 7
- 239000003795 chemical substances by application Substances 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 150000002825 nitriles Chemical class 0.000 claims 5
- 102000030595 Glucokinase Human genes 0.000 claims 4
- 108010021582 Glucokinase Proteins 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 4
- 230000003449 preventive effect Effects 0.000 claims 4
- 208000008589 Obesity Diseases 0.000 claims 3
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229940124828 glucokinase activator Drugs 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 201000001421 hyperglycemia Diseases 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 3
- 150000003536 tetrazoles Chemical class 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 3
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims 2
- VSWXAFBANQPLTL-UHFFFAOYSA-N 1-(2,4-difluorophenoxy)cyclopropane-1-carboxylic acid Chemical compound C=1C=C(F)C=C(F)C=1OC1(C(=O)O)CC1 VSWXAFBANQPLTL-UHFFFAOYSA-N 0.000 claims 2
- DJQBVNCLTRXLNX-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-(4-methylsulfonylphenyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound N=1C=CSC=1NC(=O)C(C=1C=CC(=CC=1)S(C)(=O)=O)(C)OC1=CC=C(F)C=C1F DJQBVNCLTRXLNX-UHFFFAOYSA-N 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 230000002218 hypoglycaemic effect Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 230000001105 regulatory effect Effects 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- MPTCPWOTFUIXKN-UHFFFAOYSA-N 1-(4-methylsulfonylphenoxy)cyclohexane-1-carboxylic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC1(C(O)=O)CCCCC1 MPTCPWOTFUIXKN-UHFFFAOYSA-N 0.000 claims 1
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 1
- ZOEMMIPWAOBULA-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yloxy)-2-(4-methylsulfonylphenyl)-n-(4-phenyl-1,3-thiazol-2-yl)propanamide Chemical compound C=1C=C2OCOC2=CC=1OC(C)(C=1C=CC(=CC=1)S(C)(=O)=O)C(=O)NC(SC=1)=NC=1C1=CC=CC=C1 ZOEMMIPWAOBULA-UHFFFAOYSA-N 0.000 claims 1
- WCBOKFRITPYWOZ-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yloxy)-n-(5-chloro-1,3-thiazol-2-yl)-2-[4-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=C2OCOC2=CC=1OC(C)(C=1C=CC(=CC=1)C(F)(F)F)C(=O)NC1=NC=C(Cl)S1 WCBOKFRITPYWOZ-UHFFFAOYSA-N 0.000 claims 1
- RNPRYZFOUDIKEY-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yloxy)-n-(5-chloro-1,3-thiazol-2-yl)-2-methylpropanamide Chemical compound C=1C=C2OCOC2=CC=1OC(C)(C)C(=O)NC1=NC=C(Cl)S1 RNPRYZFOUDIKEY-UHFFFAOYSA-N 0.000 claims 1
- RVSKNIYVTVIMKA-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yloxy)-n-(5-fluoro-1,3-thiazol-2-yl)-2-(4-methylsulfonylphenyl)propanamide Chemical compound C=1C=C2OCOC2=CC=1OC(C)(C=1C=CC(=CC=1)S(C)(=O)=O)C(=O)NC1=NC=C(F)S1 RVSKNIYVTVIMKA-UHFFFAOYSA-N 0.000 claims 1
- IMNMHPHINRXMBI-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yloxy)-n-[4-[2-(4-fluoroanilino)-2-oxoethyl]-1,3-thiazol-2-yl]-2-methylpropanamide Chemical compound C=1C=C2OCOC2=CC=1OC(C)(C)C(=O)NC(SC=1)=NC=1CC(=O)NC1=CC=C(F)C=C1 IMNMHPHINRXMBI-UHFFFAOYSA-N 0.000 claims 1
- KMFDTCAGZDDFHJ-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yloxy)-n-[4-[2-(4-fluorophenoxy)ethyl]-1,3-thiazol-2-yl]-2-methylpropanamide Chemical compound C=1C=C2OCOC2=CC=1OC(C)(C)C(=O)NC(SC=1)=NC=1CCOC1=CC=C(F)C=C1 KMFDTCAGZDDFHJ-UHFFFAOYSA-N 0.000 claims 1
- YICALPKJIQUZDM-UHFFFAOYSA-N 2-(1h-indol-5-yloxy)-2-(4-methylsulfonylphenyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C=1C=C2NC=CC2=CC=1OC(C)(C=1C=CC(=CC=1)S(C)(=O)=O)C(=O)NC1=NC=CS1 YICALPKJIQUZDM-UHFFFAOYSA-N 0.000 claims 1
- XENKQFZHURVGAI-UHFFFAOYSA-N 2-(1h-indol-5-yloxy)-2-methyl-n-(1,3-thiazol-2-yl)propanamide Chemical compound C=1C=C2NC=CC2=CC=1OC(C)(C)C(=O)NC1=NC=CS1 XENKQFZHURVGAI-UHFFFAOYSA-N 0.000 claims 1
- ICABLDLYXDFLQN-UHFFFAOYSA-N 2-(2,3-dihydro-1h-inden-5-yloxy)-2-methyl-n-(1,3-thiazol-2-yl)propanamide Chemical compound C=1C=C2CCCC2=CC=1OC(C)(C)C(=O)NC1=NC=CS1 ICABLDLYXDFLQN-UHFFFAOYSA-N 0.000 claims 1
- OMZLBDOBPXRQPM-UHFFFAOYSA-N 2-(2,4-difluoroanilino)-2-(4-methylsulfonylphenyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound N=1C=CSC=1NC(=O)C(C=1C=CC(=CC=1)S(C)(=O)=O)(C)NC1=CC=C(F)C=C1F OMZLBDOBPXRQPM-UHFFFAOYSA-N 0.000 claims 1
- AOQUEZCCRYYXAS-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-(4-methylsulfonylphenyl)-n-(1h-pyrazol-5-yl)propanamide Chemical compound C1=CNN=C1NC(=O)C(C=1C=CC(=CC=1)S(C)(=O)=O)(C)OC1=CC=C(F)C=C1F AOQUEZCCRYYXAS-UHFFFAOYSA-N 0.000 claims 1
- LOGGGMXRGAPMSI-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-(4-methylsulfonylphenyl)-n-(4-phenyl-1,3-thiazol-2-yl)propanamide Chemical compound N=1C(C=2C=CC=CC=2)=CSC=1NC(=O)C(C=1C=CC(=CC=1)S(C)(=O)=O)(C)OC1=CC=C(F)C=C1F LOGGGMXRGAPMSI-UHFFFAOYSA-N 0.000 claims 1
- GCOWBPPNTGBRSW-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-(4-methylsulfonylphenyl)-n-(5-methyl-1,3-thiazol-2-yl)propanamide Chemical compound S1C(C)=CN=C1NC(=O)C(C)(C=1C=CC(=CC=1)S(C)(=O)=O)OC1=CC=C(F)C=C1F GCOWBPPNTGBRSW-UHFFFAOYSA-N 0.000 claims 1
- LAJALFSCYCUAQD-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-(4-methylsulfonylphenyl)-n-(5-phenyl-1,3,4-thiadiazol-2-yl)propanamide Chemical compound N=1N=C(C=2C=CC=CC=2)SC=1NC(=O)C(C=1C=CC(=CC=1)S(C)(=O)=O)(C)OC1=CC=C(F)C=C1F LAJALFSCYCUAQD-UHFFFAOYSA-N 0.000 claims 1
- USWMVAVBTBFYLZ-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-(4-methylsulfonylphenyl)-n-pyrazin-2-ylpropanamide Chemical compound C=1N=CC=NC=1NC(=O)C(C=1C=CC(=CC=1)S(C)(=O)=O)(C)OC1=CC=C(F)C=C1F USWMVAVBTBFYLZ-UHFFFAOYSA-N 0.000 claims 1
- VCXKTRKSVHHZHJ-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-(4-methylsulfonylphenyl)-n-pyrimidin-2-ylpropanamide Chemical compound N=1C=CC=NC=1NC(=O)C(C=1C=CC(=CC=1)S(C)(=O)=O)(C)OC1=CC=C(F)C=C1F VCXKTRKSVHHZHJ-UHFFFAOYSA-N 0.000 claims 1
- TWLRWYGVHCWNOC-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-methyl-n-(1,2-oxazol-3-yl)propanamide Chemical compound C1=CON=C1NC(=O)C(C)(C)OC1=CC=C(F)C=C1F TWLRWYGVHCWNOC-UHFFFAOYSA-N 0.000 claims 1
- CDCHAKAQRPKVOR-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-methyl-n-(1,3,4-thiadiazol-2-yl)propanamide Chemical compound N=1N=CSC=1NC(=O)C(C)(C)OC1=CC=C(F)C=C1F CDCHAKAQRPKVOR-UHFFFAOYSA-N 0.000 claims 1
- YIBXCHVPRCTEKH-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-methyl-n-(1,3-thiazol-2-yl)-4-thiophen-3-ylbutanamide Chemical compound C=1C=C(F)C=C(F)C=1OC(C(=O)NC=1SC=CN=1)(C)CCC=1C=CSC=1 YIBXCHVPRCTEKH-UHFFFAOYSA-N 0.000 claims 1
- AYVLPTUBTPSKOW-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-methyl-n-(1,3-thiazol-2-yl)propanamide Chemical compound N=1C=CSC=1NC(=O)C(C)(C)OC1=CC=C(F)C=C1F AYVLPTUBTPSKOW-UHFFFAOYSA-N 0.000 claims 1
- KIFDYZJAYSUXLK-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-methyl-n-(2h-tetrazol-5-yl)propanamide Chemical compound N=1N=NNC=1NC(=O)C(C)(C)OC1=CC=C(F)C=C1F KIFDYZJAYSUXLK-UHFFFAOYSA-N 0.000 claims 1
- PPQCWARFAYXMNP-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-methyl-n-(4-methylpyrimidin-2-yl)propanamide Chemical compound CC1=CC=NC(NC(=O)C(C)(C)OC=2C(=CC(F)=CC=2)F)=N1 PPQCWARFAYXMNP-UHFFFAOYSA-N 0.000 claims 1
- UEIGAFMBSMXJPR-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-methyl-n-(4-phenyl-1,3-thiazol-2-yl)butanamide Chemical compound N=1C(C=2C=CC=CC=2)=CSC=1NC(=O)C(C)(CC)OC1=CC=C(F)C=C1F UEIGAFMBSMXJPR-UHFFFAOYSA-N 0.000 claims 1
- TXQZYRHIHBKENR-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-methyl-n-(4-phenyl-1,3-thiazol-2-yl)propanamide Chemical compound N=1C(C=2C=CC=CC=2)=CSC=1NC(=O)C(C)(C)OC1=CC=C(F)C=C1F TXQZYRHIHBKENR-UHFFFAOYSA-N 0.000 claims 1
- HRTWTBSZCAOKKG-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-methyl-n-[4-(trifluoromethyl)-1,3-thiazol-2-yl]propanamide Chemical compound N=1C(C(F)(F)F)=CSC=1NC(=O)C(C)(C)OC1=CC=C(F)C=C1F HRTWTBSZCAOKKG-UHFFFAOYSA-N 0.000 claims 1
- AFGIBTGWCHKRGY-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-methyl-n-[4-[2-oxo-2-(1,3-thiazol-2-ylamino)ethyl]-1,3-thiazol-2-yl]propanamide Chemical compound N=1C(CC(=O)NC=2SC=CN=2)=CSC=1NC(=O)C(C)(C)OC1=CC=C(F)C=C1F AFGIBTGWCHKRGY-UHFFFAOYSA-N 0.000 claims 1
- IQPWTMDSNHXMLZ-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-2-methyl-n-[4-[2-oxo-2-(pyridin-3-ylamino)ethyl]-1,3-thiazol-2-yl]butanamide Chemical compound N=1C(CC(=O)NC=2C=NC=CC=2)=CSC=1NC(=O)C(C)(CC)OC1=CC=C(F)C=C1F IQPWTMDSNHXMLZ-UHFFFAOYSA-N 0.000 claims 1
- UETWKIDOBQOBFT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-(4-methylpyrimidin-2-yl)-2-(4-methylsulfonylphenyl)propanamide Chemical compound CC1=CC=NC(NC(=O)C(C)(OC=2C(=CC(F)=CC=2)F)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 UETWKIDOBQOBFT-UHFFFAOYSA-N 0.000 claims 1
- ANRVYNFUUQKWGY-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-(5-fluoro-1,3-thiazol-2-yl)-2-(4-methylsulfonylphenyl)propanamide Chemical compound N=1C=C(F)SC=1NC(=O)C(C=1C=CC(=CC=1)S(C)(=O)=O)(C)OC1=CC=C(F)C=C1F ANRVYNFUUQKWGY-UHFFFAOYSA-N 0.000 claims 1
- NJKUHDQXXQLKSP-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-(5-fluoro-1,3-thiazol-2-yl)-2-[4-(oxan-4-ylsulfonyl)phenyl]propanamide Chemical compound N=1C=C(F)SC=1NC(=O)C(C=1C=CC(=CC=1)S(=O)(=O)C1CCOCC1)(C)OC1=CC=C(F)C=C1F NJKUHDQXXQLKSP-UHFFFAOYSA-N 0.000 claims 1
- CCIHPDYQOPTKBX-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-(5-fluoro-1,3-thiazol-2-yl)-2-methylbutanamide Chemical compound N=1C=C(F)SC=1NC(=O)C(C)(CC)OC1=CC=C(F)C=C1F CCIHPDYQOPTKBX-UHFFFAOYSA-N 0.000 claims 1
- NYYLSMJRVFGCIN-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-(5-fluoro-1,3-thiazol-2-yl)-2-methylpropanamide Chemical compound N=1C=C(F)SC=1NC(=O)C(C)(C)OC1=CC=C(F)C=C1F NYYLSMJRVFGCIN-UHFFFAOYSA-N 0.000 claims 1
- KMBYTMNRBFKGCR-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-(6-fluoro-1,3-benzothiazol-2-yl)-2-(4-methylsulfonylphenyl)propanamide Chemical compound N=1C2=CC=C(F)C=C2SC=1NC(=O)C(C=1C=CC(=CC=1)S(C)(=O)=O)(C)OC1=CC=C(F)C=C1F KMBYTMNRBFKGCR-UHFFFAOYSA-N 0.000 claims 1
- LGINAKMWYWCUEB-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-(6-fluoro-1,3-benzothiazol-2-yl)-2-methylbutanamide Chemical compound N=1C2=CC=C(F)C=C2SC=1NC(=O)C(C)(CC)OC1=CC=C(F)C=C1F LGINAKMWYWCUEB-UHFFFAOYSA-N 0.000 claims 1
- KBPCIEOTVDWQLZ-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-(6-fluoro-1,3-benzothiazol-2-yl)-2-methylpropanamide Chemical compound N=1C2=CC=C(F)C=C2SC=1NC(=O)C(C)(C)OC1=CC=C(F)C=C1F KBPCIEOTVDWQLZ-UHFFFAOYSA-N 0.000 claims 1
- RBSGEQQZSVQOAC-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-[4-[2-(4-fluoroanilino)-2-oxoethyl]-1,3-thiazol-2-yl]-2-methylbutanamide Chemical compound N=1C(CC(=O)NC=2C=CC(F)=CC=2)=CSC=1NC(=O)C(C)(CC)OC1=CC=C(F)C=C1F RBSGEQQZSVQOAC-UHFFFAOYSA-N 0.000 claims 1
- UDSUTIZJVOEEKI-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-[4-[2-(4-fluoroanilino)-2-oxoethyl]-1,3-thiazol-2-yl]-2-methylpropanamide Chemical compound N=1C(CC(=O)NC=2C=CC(F)=CC=2)=CSC=1NC(=O)C(C)(C)OC1=CC=C(F)C=C1F UDSUTIZJVOEEKI-UHFFFAOYSA-N 0.000 claims 1
- KCLYZGBBOLIULP-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-[4-[2-(4-fluorophenoxy)ethyl]-1,3-thiazol-2-yl]-2-methylpropanamide Chemical compound N=1C(CCOC=2C=CC(F)=CC=2)=CSC=1NC(=O)C(C)(C)OC1=CC=C(F)C=C1F KCLYZGBBOLIULP-UHFFFAOYSA-N 0.000 claims 1
- KLFRFNFHMJHBPC-UHFFFAOYSA-N 2-(2-chloropyridin-3-yl)oxy-n-(5-chloro-1,3-thiazol-2-yl)-2-methylpropanamide Chemical compound N=1C=C(Cl)SC=1NC(=O)C(C)(C)OC1=CC=CN=C1Cl KLFRFNFHMJHBPC-UHFFFAOYSA-N 0.000 claims 1
- YYVVWOUVQVTRKJ-UHFFFAOYSA-N 2-(2h-1,2-benzoxazin-6-yloxy)-2-methyl-n-(1,3-thiazol-2-yl)propanamide Chemical compound C=1C=C2ONC=CC2=CC=1OC(C)(C)C(=O)NC1=NC=CS1 YYVVWOUVQVTRKJ-UHFFFAOYSA-N 0.000 claims 1
- LFNIVGPZONECLP-UHFFFAOYSA-N 2-(3,4-dichlorophenoxy)-n-[4-[2-(4-fluorophenoxy)ethyl]-1,3-thiazol-2-yl]-2-methylpropanamide Chemical compound N=1C(CCOC=2C=CC(F)=CC=2)=CSC=1NC(=O)C(C)(C)OC1=CC=C(Cl)C(Cl)=C1 LFNIVGPZONECLP-UHFFFAOYSA-N 0.000 claims 1
- AUSXEHHFTKWTDH-UHFFFAOYSA-N 2-(3,4-difluorophenoxy)-2-methyl-n-(1,2-oxazol-3-yl)propanamide Chemical compound C1=CON=C1NC(=O)C(C)(C)OC1=CC=C(F)C(F)=C1 AUSXEHHFTKWTDH-UHFFFAOYSA-N 0.000 claims 1
- KRFPMFWAMOLAGQ-UHFFFAOYSA-N 2-(3-acetamidophenoxy)-2-methyl-n-(1,3-thiazol-2-yl)propanamide Chemical compound CC(=O)NC1=CC=CC(OC(C)(C)C(=O)NC=2SC=CN=2)=C1 KRFPMFWAMOLAGQ-UHFFFAOYSA-N 0.000 claims 1
- YNNOCGNDUMKSNC-UHFFFAOYSA-N 2-(3-acetamidophenoxy)-n-(5-chloro-1,3-thiazol-2-yl)-2-methylpropanamide Chemical compound CC(=O)NC1=CC=CC(OC(C)(C)C(=O)NC=2SC(Cl)=CN=2)=C1 YNNOCGNDUMKSNC-UHFFFAOYSA-N 0.000 claims 1
- NCBNWXBPSYJNCM-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2,5-dimethyl-n-(1,3-thiazol-2-yl)hexanamide Chemical compound N=1C=CSC=1NC(=O)C(C)(CCC(C)C)OC1=CC=C(Cl)C=C1 NCBNWXBPSYJNCM-UHFFFAOYSA-N 0.000 claims 1
- INNDYPHLNFLRBX-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methyl-n-(1,3-thiazol-2-yl)-4-thiophen-3-ylbutanamide Chemical compound C=1C=C(Cl)C=CC=1OC(C(=O)NC=1SC=CN=1)(C)CCC=1C=CSC=1 INNDYPHLNFLRBX-UHFFFAOYSA-N 0.000 claims 1
- LIYKMEVZIOOVLZ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methyl-n-(1,3-thiazol-2-yl)propanamide Chemical compound N=1C=CSC=1NC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 LIYKMEVZIOOVLZ-UHFFFAOYSA-N 0.000 claims 1
- DFQOFIDESDKRKS-UHFFFAOYSA-N 2-(4-chlorophenoxy)-4-(4-fluorophenyl)-2-methyl-n-(1,3-thiazol-2-yl)butanamide Chemical compound C=1C=C(Cl)C=CC=1OC(C(=O)NC=1SC=CN=1)(C)CCC1=CC=C(F)C=C1 DFQOFIDESDKRKS-UHFFFAOYSA-N 0.000 claims 1
- LCQIVDIEPAUFHR-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-(5-chloro-1,3-thiazol-2-yl)-2-(4-methylsulfonylphenyl)propanamide Chemical compound N=1C=C(Cl)SC=1NC(=O)C(C=1C=CC(=CC=1)S(C)(=O)=O)(C)OC1=CC=C(Cl)C=C1 LCQIVDIEPAUFHR-UHFFFAOYSA-N 0.000 claims 1
- AWFMDUTUMHKFGB-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-(5-chloro-1,3-thiazol-2-yl)-2-methyl-4-thiophen-2-ylbutanamide Chemical compound C=1C=C(Cl)C=CC=1OC(C(=O)NC=1SC(Cl)=CN=1)(C)CCC1=CC=CS1 AWFMDUTUMHKFGB-UHFFFAOYSA-N 0.000 claims 1
- GVAOEPKDMFPCOF-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanyl-2-(4-methylsulfonylphenyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound N=1C=CSC=1NC(=O)C(C=1C=CC(=CC=1)S(C)(=O)=O)(C)SC1=CC=C(Cl)C=C1 GVAOEPKDMFPCOF-UHFFFAOYSA-N 0.000 claims 1
- ISYBRFIYRAPJEY-UHFFFAOYSA-N 2-(4-fluorophenyl)sulfanyl-2-methyl-n-(1,3-thiazol-2-yl)propanamide Chemical compound N=1C=CSC=1NC(=O)C(C)(C)SC1=CC=C(F)C=C1 ISYBRFIYRAPJEY-UHFFFAOYSA-N 0.000 claims 1
- IZHQOSOHGZYYJH-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-2-(4-phenylphenoxy)-n-(1,3-thiazol-2-yl)propanamide Chemical compound N=1C=CSC=1NC(=O)C(C=1C=CC(=CC=1)S(C)(=O)=O)(C)OC(C=C1)=CC=C1C1=CC=CC=C1 IZHQOSOHGZYYJH-UHFFFAOYSA-N 0.000 claims 1
- CFGXLPAOARLJSR-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-n-(1,3-thiazol-2-yl)-2-[5-(trifluoromethoxy)pyridin-2-yl]oxypropanamide Chemical compound N=1C=CSC=1NC(=O)C(C=1C=CC(=CC=1)S(C)(=O)=O)(C)OC1=CC=C(OC(F)(F)F)C=N1 CFGXLPAOARLJSR-UHFFFAOYSA-N 0.000 claims 1
- MXCIXAUFLYEISO-UHFFFAOYSA-N 2-(5-chloropyridin-3-yl)oxy-n-(5-chloro-1,3-thiazol-2-yl)-2-methylpropanamide Chemical compound N=1C=C(Cl)SC=1NC(=O)C(C)(C)OC1=CN=CC(Cl)=C1 MXCIXAUFLYEISO-UHFFFAOYSA-N 0.000 claims 1
- MNOLKXYYVAJQIS-UHFFFAOYSA-N 2-(5-chloropyridin-3-yl)oxy-n-[4-[2-(4-fluoroanilino)-2-oxoethyl]-1,3-thiazol-2-yl]-2-methylpropanamide Chemical compound N=1C(CC(=O)NC=2C=CC(F)=CC=2)=CSC=1NC(=O)C(C)(C)OC1=CN=CC(Cl)=C1 MNOLKXYYVAJQIS-UHFFFAOYSA-N 0.000 claims 1
- YKFZUDZMPBFIIL-UHFFFAOYSA-N 2-(6-chloropyridin-2-yl)oxy-2-methyl-n-(1,3-thiazol-2-yl)propanamide Chemical compound N=1C=CSC=1NC(=O)C(C)(C)OC1=CC=CC(Cl)=N1 YKFZUDZMPBFIIL-UHFFFAOYSA-N 0.000 claims 1
- HTLWNMBVZSEXFF-UHFFFAOYSA-N 2-(6-chloropyridin-2-yl)oxy-n-[3-(methanesulfonamido)pyridin-2-yl]-2-methylpropanamide Chemical compound N=1C=CC=C(NS(C)(=O)=O)C=1NC(=O)C(C)(C)OC1=CC=CC(Cl)=N1 HTLWNMBVZSEXFF-UHFFFAOYSA-N 0.000 claims 1
- LILSULIBVAWEMC-UHFFFAOYSA-N 2-[2-[(2-methyl-2-naphthalen-1-yloxypropanoyl)amino]-1,3-thiazol-4-yl]acetic acid Chemical compound C=1C=CC2=CC=CC=C2C=1OC(C)(C)C(=O)NC1=NC(CC(O)=O)=CS1 LILSULIBVAWEMC-UHFFFAOYSA-N 0.000 claims 1
- ICWASQOUUWCANF-UHFFFAOYSA-N 2-[2-[(2-methyl-2-naphthalen-2-yloxypropanoyl)amino]-1,3-thiazol-4-yl]acetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1OC(C)(C)C(=O)NC1=NC(CC(O)=O)=CS1 ICWASQOUUWCANF-UHFFFAOYSA-N 0.000 claims 1
- AYQNTACRSOPPSV-UHFFFAOYSA-N 2-[2-[[1-(2,4-difluorophenoxy)cyclobutanecarbonyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound OC(=O)CC1=CSC(NC(=O)C2(CCC2)OC=2C(=CC(F)=CC=2)F)=N1 AYQNTACRSOPPSV-UHFFFAOYSA-N 0.000 claims 1
- WGVGZRMVRUGIDK-UHFFFAOYSA-N 2-[2-[[1-(4-methylsulfonylphenoxy)cyclohexanecarbonyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC1(C(=O)NC=2SC=C(CC(O)=O)N=2)CCCCC1 WGVGZRMVRUGIDK-UHFFFAOYSA-N 0.000 claims 1
- BEYLAFMFSJNPAR-UHFFFAOYSA-N 2-[2-[[2-(1,3-benzodioxol-5-yloxy)-2-methylpropanoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound C=1C=C2OCOC2=CC=1OC(C)(C)C(=O)NC1=NC(CC(O)=O)=CS1 BEYLAFMFSJNPAR-UHFFFAOYSA-N 0.000 claims 1
- GGOXIYVTDXUCGA-UHFFFAOYSA-N 2-[2-[[2-(1,3-benzodioxol-5-yloxy)-2-methylpropanoyl]amino]-5-chloro-1,3-thiazol-4-yl]acetic acid Chemical compound C=1C=C2OCOC2=CC=1OC(C)(C)C(=O)NC1=NC(CC(O)=O)=C(Cl)S1 GGOXIYVTDXUCGA-UHFFFAOYSA-N 0.000 claims 1
- DWTJGGRLBLPBEX-UHFFFAOYSA-N 2-[2-[[2-(2,4-difluorophenoxy)-2-methylbutanoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=CSC=1NC(=O)C(C)(CC)OC1=CC=C(F)C=C1F DWTJGGRLBLPBEX-UHFFFAOYSA-N 0.000 claims 1
- FFNRFQUESGSKHR-UHFFFAOYSA-N 2-[2-[[2-(2,4-difluorophenoxy)-2-methylpropanoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=CSC=1NC(=O)C(C)(C)OC1=CC=C(F)C=C1F FFNRFQUESGSKHR-UHFFFAOYSA-N 0.000 claims 1
- LCSHKPXPZGAWSR-UHFFFAOYSA-N 2-[2-[[2-(4-acetamidophenoxy)-2-methylpropanoyl]amino]-5-chloro-1,3-thiazol-4-yl]acetic acid Chemical compound C1=CC(NC(=O)C)=CC=C1OC(C)(C)C(=O)NC1=NC(CC(O)=O)=C(Cl)S1 LCSHKPXPZGAWSR-UHFFFAOYSA-N 0.000 claims 1
- CDZRWCKGPBIVPB-UHFFFAOYSA-N 2-[2-[[2-(4-chlorophenoxy)-3-cyclopentyl-2-methylpropanoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound C=1C=C(Cl)C=CC=1OC(C(=O)NC=1SC=C(CC(O)=O)N=1)(C)CC1CCCC1 CDZRWCKGPBIVPB-UHFFFAOYSA-N 0.000 claims 1
- LNUYSEJHQWXCOF-UHFFFAOYSA-N 2-[2-[[2-(4-cyclohexylsulfonylphenyl)-2-(2,4-difluorophenoxy)propanoyl]amino]-5-fluoro-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=C(F)SC=1NC(=O)C(C=1C=CC(=CC=1)S(=O)(=O)C1CCCCC1)(C)OC1=CC=C(F)C=C1F LNUYSEJHQWXCOF-UHFFFAOYSA-N 0.000 claims 1
- VGGAQXHFNVASCT-UHFFFAOYSA-N 2-[2-[[2-(4-cyclopentylsulfonylphenyl)-2-(2,4-difluorophenoxy)propanoyl]amino]-5-fluoro-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=C(F)SC=1NC(=O)C(C=1C=CC(=CC=1)S(=O)(=O)C1CCCC1)(C)OC1=CC=C(F)C=C1F VGGAQXHFNVASCT-UHFFFAOYSA-N 0.000 claims 1
- QSXLWGXDZMENKM-UHFFFAOYSA-N 2-[2-[[2-(4-tert-butylphenoxy)-2-methylpropanoyl]amino]-5-chloro-1,3-thiazol-4-yl]acetic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1OC(C)(C)C(=O)NC1=NC(CC(O)=O)=C(Cl)S1 QSXLWGXDZMENKM-UHFFFAOYSA-N 0.000 claims 1
- PRFDKTLALVCBKY-UHFFFAOYSA-N 2-[2-[[2-(5-chloropyridin-2-yl)oxy-2-methylpropanoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=CSC=1NC(=O)C(C)(C)OC1=CC=C(Cl)C=N1 PRFDKTLALVCBKY-UHFFFAOYSA-N 0.000 claims 1
- YSCQMTSGJCXLGD-UHFFFAOYSA-N 2-[2-[[2-(6-chloropyridin-3-yl)oxy-2-(4-cyclopropylsulfonylphenyl)propanoyl]amino]-5-fluoro-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=C(F)SC=1NC(=O)C(C=1C=CC(=CC=1)S(=O)(=O)C1CC1)(C)OC1=CC=C(Cl)N=C1 YSCQMTSGJCXLGD-UHFFFAOYSA-N 0.000 claims 1
- YJMCURAKOSRHOJ-UHFFFAOYSA-N 2-[2-[[2-(6-chloropyridin-3-yl)oxy-2-(4-methylsulfonylphenyl)propanoyl]amino]-5-fluoro-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=C(F)SC=1NC(=O)C(C=1C=CC(=CC=1)S(C)(=O)=O)(C)OC1=CC=C(Cl)N=C1 YJMCURAKOSRHOJ-UHFFFAOYSA-N 0.000 claims 1
- YVFHKLTWTJMHCH-UHFFFAOYSA-N 2-[2-[[2-methyl-2-(4-methylsulfonylphenoxy)propanoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=CSC=1NC(=O)C(C)(C)OC1=CC=C(S(C)(=O)=O)C=C1 YVFHKLTWTJMHCH-UHFFFAOYSA-N 0.000 claims 1
- LCYHAVQZYAAHEU-UHFFFAOYSA-N 2-[2-chloro-5-(2-thiophen-3-ylethoxy)phenoxy]-2-methyl-n-(1,3-thiazol-2-yl)propanamide Chemical compound N=1C=CSC=1NC(=O)C(C)(C)OC(C(=CC=1)Cl)=CC=1OCCC=1C=CSC=1 LCYHAVQZYAAHEU-UHFFFAOYSA-N 0.000 claims 1
- AYWFUAYJAHWKFC-UHFFFAOYSA-N 2-[3-(methanesulfonamido)phenoxy]-2-methyl-n-(1,3-thiazol-2-yl)propanamide Chemical compound N=1C=CSC=1NC(=O)C(C)(C)OC1=CC=CC(NS(C)(=O)=O)=C1 AYWFUAYJAHWKFC-UHFFFAOYSA-N 0.000 claims 1
- RKMATNAAHHJPPQ-UHFFFAOYSA-N 2-[4-(2,5-dimethylpyrrol-1-yl)phenoxy]-2-methyl-n-(1,3-thiazol-2-yl)propanamide Chemical compound CC1=CC=C(C)N1C(C=C1)=CC=C1OC(C)(C)C(=O)NC1=NC=CS1 RKMATNAAHHJPPQ-UHFFFAOYSA-N 0.000 claims 1
- RYCQFNOBAGDXTL-UHFFFAOYSA-N 2-[4-[1-[(5-chloro-1,3-thiazol-2-yl)amino]-2-methyl-1-oxopropan-2-yl]oxy-3-fluorophenyl]acetic acid Chemical compound N=1C=C(Cl)SC=1NC(=O)C(C)(C)OC1=CC=C(CC(O)=O)C=C1F RYCQFNOBAGDXTL-UHFFFAOYSA-N 0.000 claims 1
- SLFQBKQPIVPJCL-UHFFFAOYSA-N 2-[4-chloro-3-(2-thiophen-3-ylethoxy)phenoxy]-2-methyl-n-(1,3-thiazol-2-yl)propanamide Chemical compound N=1C=CSC=1NC(=O)C(C)(C)OC(C=1)=CC=C(Cl)C=1OCCC=1C=CSC=1 SLFQBKQPIVPJCL-UHFFFAOYSA-N 0.000 claims 1
- WUKGSDIMYIYXOQ-UHFFFAOYSA-N 2-[5-chloro-2-[[1-(2,4-difluorophenoxy)cyclopropanecarbonyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound S1C(Cl)=C(CC(=O)O)N=C1NC(=O)C1(OC=2C(=CC(F)=CC=2)F)CC1 WUKGSDIMYIYXOQ-UHFFFAOYSA-N 0.000 claims 1
- MQWNQMRVHIXUPE-UHFFFAOYSA-N 2-[5-chloro-2-[[2-(2,4-difluorophenoxy)-2-(4-methylsulfonylphenyl)propanoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=C(Cl)SC=1NC(=O)C(C=1C=CC(=CC=1)S(C)(=O)=O)(C)OC1=CC=C(F)C=C1F MQWNQMRVHIXUPE-UHFFFAOYSA-N 0.000 claims 1
- VWISSHKACIMAJY-UHFFFAOYSA-N 2-[5-chloro-2-[[2-(2,4-difluorophenoxy)-2-methylpropanoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=C(Cl)SC=1NC(=O)C(C)(C)OC1=CC=C(F)C=C1F VWISSHKACIMAJY-UHFFFAOYSA-N 0.000 claims 1
- BYZZUWQNUNLLQA-UHFFFAOYSA-N 2-[5-chloro-2-[[2-(2,5-difluorophenoxy)-2-methylpropanoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=C(Cl)SC=1NC(=O)C(C)(C)OC1=CC(F)=CC=C1F BYZZUWQNUNLLQA-UHFFFAOYSA-N 0.000 claims 1
- IMIQJUUVYIBGNA-UHFFFAOYSA-N 2-[5-chloro-2-[[2-(2,6-difluorophenoxy)-2-methylpropanoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=C(Cl)SC=1NC(=O)C(C)(C)OC1=C(F)C=CC=C1F IMIQJUUVYIBGNA-UHFFFAOYSA-N 0.000 claims 1
- UJJOUEZRMSGTEV-UHFFFAOYSA-N 2-[5-chloro-2-[[2-(3,4-difluorophenoxy)-2-methylpropanoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=C(Cl)SC=1NC(=O)C(C)(C)OC1=CC=C(F)C(F)=C1 UJJOUEZRMSGTEV-UHFFFAOYSA-N 0.000 claims 1
- DFABWEKOQONDKQ-UHFFFAOYSA-N 2-[5-chloro-2-[[2-(4-chlorophenoxy)-2-methylpropanoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=C(Cl)SC=1NC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 DFABWEKOQONDKQ-UHFFFAOYSA-N 0.000 claims 1
- LBZSEFRELSCKPC-UHFFFAOYSA-N 2-[5-chloro-2-[[2-(4-fluorophenoxy)-2-(4-methylsulfonylphenyl)propanoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=C(Cl)SC=1NC(=O)C(C=1C=CC(=CC=1)S(C)(=O)=O)(C)OC1=CC=C(F)C=C1 LBZSEFRELSCKPC-UHFFFAOYSA-N 0.000 claims 1
- UNTIMQFDKRBZSJ-UHFFFAOYSA-N 2-[5-chloro-2-[[2-methyl-2-(3-nitrophenoxy)propanoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=C(Cl)SC=1NC(=O)C(C)(C)OC1=CC=CC([N+]([O-])=O)=C1 UNTIMQFDKRBZSJ-UHFFFAOYSA-N 0.000 claims 1
- RSXONDHMAINALI-UHFFFAOYSA-N 2-[5-chloro-2-[[2-methyl-2-(4-nitrophenoxy)propanoyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound N=1C(CC(O)=O)=C(Cl)SC=1NC(=O)C(C)(C)OC1=CC=C([N+]([O-])=O)C=C1 RSXONDHMAINALI-UHFFFAOYSA-N 0.000 claims 1
- KITGCKQZQNIKHD-UHFFFAOYSA-N 2-[[1-(4-methylsulfonylphenoxy)cyclohexanecarbonyl]amino]-1,3-thiazole-4-carboxylic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC1(C(=O)NC=2SC=C(N=2)C(O)=O)CCCCC1 KITGCKQZQNIKHD-UHFFFAOYSA-N 0.000 claims 1
- QWRCXDQOAWBXRQ-UHFFFAOYSA-N 2-[[2-(1,3-benzodioxol-5-yloxy)-2-methylpropanoyl]amino]-1,3-thiazole-4-carboxylic acid Chemical compound C=1C=C2OCOC2=CC=1OC(C)(C)C(=O)NC1=NC(C(O)=O)=CS1 QWRCXDQOAWBXRQ-UHFFFAOYSA-N 0.000 claims 1
- ZTPKDCYAQDEMOT-UHFFFAOYSA-N 2-[[2-(1,3-benzodioxol-5-yloxy)-2-methylpropanoyl]amino]-5-chloro-1,3-thiazole-4-carboxylic acid Chemical compound C=1C=C2OCOC2=CC=1OC(C)(C)C(=O)NC1=NC(C(O)=O)=C(Cl)S1 ZTPKDCYAQDEMOT-UHFFFAOYSA-N 0.000 claims 1
- JIBHCPNYWLIUII-UHFFFAOYSA-N 2-[[2-(2,4-difluorophenoxy)-2-(4-methylsulfonylphenyl)propanoyl]amino]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(C)N=C1NC(=O)C(C)(C=1C=CC(=CC=1)S(C)(=O)=O)OC1=CC=C(F)C=C1F JIBHCPNYWLIUII-UHFFFAOYSA-N 0.000 claims 1
- PMRSWIYOZBUYGM-UHFFFAOYSA-N 2-[[2-(2,4-difluorophenoxy)-2-methylpropanoyl]amino]-1,3-thiazole-4-carboxylic acid Chemical compound N=1C(C(O)=O)=CSC=1NC(=O)C(C)(C)OC1=CC=C(F)C=C1F PMRSWIYOZBUYGM-UHFFFAOYSA-N 0.000 claims 1
- NRQQMXONPAQVIS-UHFFFAOYSA-N 2-[[2-(2,4-difluorophenoxy)-2-methylpropanoyl]amino]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(C)N=C1NC(=O)C(C)(C)OC1=CC=C(F)C=C1F NRQQMXONPAQVIS-UHFFFAOYSA-N 0.000 claims 1
- XDKIGDBIOBBPMW-UHFFFAOYSA-N 2-[[2-(2,4-difluorophenoxy)-2-methylpropanoyl]amino]-n-(4-fluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound N=1C(C(=O)NC=2C=CC(F)=CC=2)=CSC=1NC(=O)C(C)(C)OC1=CC=C(F)C=C1F XDKIGDBIOBBPMW-UHFFFAOYSA-N 0.000 claims 1
- OZDPQADLXDSFAI-UHFFFAOYSA-N 2-methyl-2-(3-pyrrolidin-1-ylphenoxy)-n-(1,3-thiazol-2-yl)propanamide Chemical compound N=1C=CSC=1NC(=O)C(C)(C)OC(C=1)=CC=CC=1N1CCCC1 OZDPQADLXDSFAI-UHFFFAOYSA-N 0.000 claims 1
- DCUDJIRPYDYCKY-UHFFFAOYSA-N 2-methyl-2-(4-methylsulfanylphenoxy)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=CC(SC)=CC=C1OC(C)(C)C(=O)NC1=NC=CS1 DCUDJIRPYDYCKY-UHFFFAOYSA-N 0.000 claims 1
- XEHRXXCGMZTLKA-UHFFFAOYSA-N 2-methyl-2-(4-phenoxyphenoxy)-n-(1,3-thiazol-2-yl)propanamide Chemical compound N=1C=CSC=1NC(=O)C(C)(C)OC(C=C1)=CC=C1OC1=CC=CC=C1 XEHRXXCGMZTLKA-UHFFFAOYSA-N 0.000 claims 1
- ZNQRQYXDUFJQLC-UHFFFAOYSA-N 2-methyl-2-(4-phenylphenoxy)-n-(1,3-thiazol-2-yl)propanamide Chemical compound N=1C=CSC=1NC(=O)C(C)(C)OC(C=C1)=CC=C1C1=CC=CC=C1 ZNQRQYXDUFJQLC-UHFFFAOYSA-N 0.000 claims 1
- NQKYJOSZCRIZBY-UHFFFAOYSA-N 2-methyl-2-[(3-oxo-4h-1,4-benzoxazin-7-yl)oxy]-n-(1,3-thiazol-2-yl)propanamide Chemical compound C=1C=C2NC(=O)COC2=CC=1OC(C)(C)C(=O)NC1=NC=CS1 NQKYJOSZCRIZBY-UHFFFAOYSA-N 0.000 claims 1
- XDTGCXWBXWKVDR-UHFFFAOYSA-N 2-methyl-2-[4-(propan-2-ylamino)phenoxy]-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=CC(NC(C)C)=CC=C1OC(C)(C)C(=O)NC1=NC=CS1 XDTGCXWBXWKVDR-UHFFFAOYSA-N 0.000 claims 1
- DQZFALIXADGDEC-UHFFFAOYSA-N 2-methyl-2-naphthalen-1-yloxy-n-(1,3-thiazol-2-yl)propanamide Chemical compound C=1C=CC2=CC=CC=C2C=1OC(C)(C)C(=O)NC1=NC=CS1 DQZFALIXADGDEC-UHFFFAOYSA-N 0.000 claims 1
- FVRLATPWEMWGMH-UHFFFAOYSA-N 2-methyl-2-naphthalen-2-yloxy-n-(1,3-thiazol-2-yl)propanamide Chemical compound C=1C=C2C=CC=CC2=CC=1OC(C)(C)C(=O)NC1=NC=CS1 FVRLATPWEMWGMH-UHFFFAOYSA-N 0.000 claims 1
- NBVRTOJRTFNZLM-UHFFFAOYSA-N 2-methyl-n-(1,3-thiazol-2-yl)-2-(4-thiophen-3-ylphenoxy)propanamide Chemical compound N=1C=CSC=1NC(=O)C(C)(C)OC(C=C1)=CC=C1C=1C=CSC=1 NBVRTOJRTFNZLM-UHFFFAOYSA-N 0.000 claims 1
- RGCKSFOUYPHKBG-UHFFFAOYSA-N 2-methyl-n-(1,3-thiazol-2-yl)-2-[3-(trifluoromethyl)anilino]propanamide Chemical compound N=1C=CSC=1NC(=O)C(C)(C)NC1=CC=CC(C(F)(F)F)=C1 RGCKSFOUYPHKBG-UHFFFAOYSA-N 0.000 claims 1
- ORHYMMHBEPGDEE-UHFFFAOYSA-N 2-methyl-n-(1,3-thiazol-2-yl)-2-[4-(2-thiophen-2-ylethylamino)phenoxy]propanamide Chemical compound N=1C=CSC=1NC(=O)C(C)(C)OC(C=C1)=CC=C1NCCC1=CC=CS1 ORHYMMHBEPGDEE-UHFFFAOYSA-N 0.000 claims 1
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| PCT/IN2008/000109 WO2008104994A2 (en) | 2007-02-28 | 2008-02-25 | 2,2,2-tri-substituted acetamide derivatives as glucokinase activators, their process and pharmaceutical application |
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| US (1) | US8940900B2 (https=) |
| EP (1) | EP2125735B1 (https=) |
| JP (1) | JP5491871B2 (https=) |
| CN (1) | CN101622231B (https=) |
| CA (1) | CA2679185A1 (https=) |
| WO (1) | WO2008104994A2 (https=) |
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| CA2657247A1 (en) | 2006-07-28 | 2008-01-31 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| US7928123B2 (en) | 2006-09-25 | 2011-04-19 | Boehringer Ingelheim International Gmbh | Compounds which modulate the CB2 receptor |
| US9340506B2 (en) | 2007-10-08 | 2016-05-17 | Advinus Therapeutics Limited | Acetamide derivatives as glucokinase activators, their process and medicinal applications |
| JP5580201B2 (ja) * | 2007-10-08 | 2014-08-27 | アドビヌス・セラピューティクス・プライベート・リミテッド | グルコキナーゼアクチベータとしてのアセトアミド誘導体、その製法及び医薬応用 |
| CA2704684A1 (en) | 2007-11-07 | 2009-05-14 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| US8178568B2 (en) | 2008-07-10 | 2012-05-15 | Boehringer Ingelheim International Gmbh | Sulfone compounds which modulate the CB2 receptor |
| CA2737639A1 (en) | 2008-09-25 | 2010-04-01 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the cb2 receptor |
| US8299103B2 (en) | 2009-06-15 | 2012-10-30 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the CB2 receptor |
| JP5756800B2 (ja) | 2009-06-16 | 2015-07-29 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｂ２受容体を調節するアゼチジン２−カルボキサミド誘導体 |
| JP2011006366A (ja) * | 2009-06-26 | 2011-01-13 | Sanwa Kagaku Kenkyusho Co Ltd | 新規チオフェンカルボキサミド誘導体及びその医薬用途 |
| WO2011037795A1 (en) | 2009-09-22 | 2011-03-31 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the cb2 receptor |
| WO2011080755A1 (en) | 2009-12-29 | 2011-07-07 | Advinus Therapeutics Private Limited | Fused nitrogen heterocyclic compounds, process of preparation and uses thereof |
| WO2011088015A1 (en) | 2010-01-15 | 2011-07-21 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| WO2011095997A1 (en) | 2010-02-08 | 2011-08-11 | Advinus Therapeutics Private Limited | Benzamide compounds as glucokinase activators and their pharmaceutical application |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8329735B2 (en) | 2010-03-05 | 2012-12-11 | Boehringer Ingelheim International Gmbh | Tetrazole compounds which selectively modulate the CB2 receptor |
| CN102959076B (zh) | 2010-03-31 | 2015-09-16 | 斯克里普斯研究所 | 重编程细胞 |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| EP2402327B1 (en) * | 2010-06-29 | 2018-03-07 | Impetis Biosciences Ltd. | Acetamide compounds as glucokinase activators, their process and medicinal applications |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| WO2012012307A1 (en) | 2010-07-22 | 2012-01-26 | Boehringer Ingelheim International Gmbh | Sulfonyl compounds which modulate the cb2 rece |
| WO2012020357A1 (en) * | 2010-08-09 | 2012-02-16 | Advinus Therapeutics Ltd. | Acetamide compounds, their process and pharmaceutical application |
| WO2012051405A1 (en) * | 2010-10-13 | 2012-04-19 | Bristol-Myers Squibb Company | Methods for preparing macrocycles and macrocycle stabilized peptides |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2803668A1 (en) | 2013-05-17 | 2014-11-19 | Boehringer Ingelheim International Gmbh | Novel (cyano-dimethyl-methyl)-isoxazoles and -[1,3,4]thiadiazoles |
| WO2015054662A1 (en) | 2013-10-10 | 2015-04-16 | Eastern Virginia Medical School | 4-((2-hydroxy-3-methoxybenzyl)amino) benzenesulfonamide derivatives as 12-lipoxygenase inhibitors |
| US10526287B2 (en) | 2015-04-23 | 2020-01-07 | Constellation Pharmaceuticals, Inc. | LSD1 inhibitors and uses thereof |
| WO2016176473A1 (en) | 2015-04-28 | 2016-11-03 | Sanford-Burnham Medical Researc Institute | Apelin receptor agonists and methods of use thereof |
| CA3026149A1 (en) | 2016-06-02 | 2017-12-07 | Cadent Therapeutics, Inc. | Potassium channel modulators |
| TWI753037B (zh) | 2016-10-26 | 2022-01-21 | 美商星座製藥公司 | Lsd1抑制劑及其用途 |
| SI3571193T1 (sl) | 2017-01-23 | 2022-04-29 | Cadent Therapeutics, Inc. | Modulatorji kalijevega kanalčka |
| AU2018300150A1 (en) | 2017-07-11 | 2020-01-30 | Vertex Pharmaceuticals Incorporated | Carboxamides as modulators of sodium channels |
| CA3116339A1 (en) | 2018-10-22 | 2020-04-30 | Cadent Therapeutics, Inc. | Crystalline forms of potassium channel modulators |
| WO2020146682A1 (en) | 2019-01-10 | 2020-07-16 | Vertex Pharmaceuticals Incorporated | Carboxamides as modulators of sodium channels |
| US12440481B2 (en) | 2019-01-10 | 2025-10-14 | Vertex Pharmaceuticals Incorporated | Esters and carbamates as modulators of sodium channels |
| CN117024749A (zh) | 2019-06-28 | 2023-11-10 | 国立大学法人东京大学 | 蛋白质内包高分子胶束 |
| JP2023533016A (ja) | 2020-07-11 | 2023-08-01 | ファイザー・インク | 抗ウイルス性ヘテロアリールケトン誘導体 |
| US11351149B2 (en) | 2020-09-03 | 2022-06-07 | Pfizer Inc. | Nitrile-containing antiviral compounds |
| WO2022160138A1 (zh) * | 2021-01-27 | 2022-08-04 | 承德医学院 | 苯并嗪-4-酮类化合物、其制备方法及医药用途 |
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| US3776917A (en) | 1972-06-05 | 1973-12-04 | Schering Corp | 2-amino-6-phenalkyl-aminopyridines and derivatives thereof |
| DE2263110B2 (de) * | 1972-12-22 | 1980-01-31 | Ludwig Merckle Kg Chem. Pharm. Fabrik, 7902 Blaubeuren | 2-Amino-4-phenyläthylamino-6-phenoxymethyl-1 ^-triazine und Verfahren zu ihrer Herstellung |
| JPS5019435A (https=) * | 1973-06-20 | 1975-02-28 | ||
| ES439155A1 (es) * | 1975-07-04 | 1977-10-16 | Funk Lab | Procedimiento de obtencion y uso de compuestos halo-fenoxi de accion farmacologica en el tratamiento de los trastornos del equilibrio lipidico. |
| GB1561350A (en) | 1976-11-05 | 1980-02-20 | May & Baker Ltd | Benzamide derivatives |
| JPS5564592A (en) | 1978-11-10 | 1980-05-15 | Teijin Ltd | Thiazolo 3, 2-a pyrimidine derivative, its preparation, and drug comprising it |
| DE2924900A1 (de) * | 1979-06-20 | 1981-01-22 | Nattermann A & Cie | Tetrazolylamide von phenoxycarbonsaeuren, verfahren zu deren herstellung und diese enthaltende neue antilipaemisch und antiatherosklerotisch wirkende arzneimittel |
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| TW257757B (https=) * | 1993-03-03 | 1995-09-21 | Boehringer Mannheim Gmbh | |
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| PL350669A1 (en) | 1999-03-29 | 2003-01-27 | Hoffmann La Roche | Glucokinase activators |
| WO2001012189A1 (en) * | 1999-08-12 | 2001-02-22 | Pharmacia Italia S.P.A. | 3(5)-amino-pyrazole derivatives, process for their preparation and their use as antitumor agents |
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| KR20020058023A (ko) | 1999-11-18 | 2002-07-12 | 한스 루돌프 하우스, 헨리테 브룬너, 베아트리체 귄터 | 살충성 아미노헤테로시클릴아미드 화합물 |
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| WO2001085707A1 (en) | 2000-05-08 | 2001-11-15 | F. Hoffmann-La Roche Ag | Para-amine substituted phenylamide glucokinase activators |
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| US7067539B2 (en) | 2001-02-08 | 2006-06-27 | Schering Corporation | Cannabinoid receptor ligands |
| SE0102764D0 (sv) * | 2001-08-17 | 2001-08-17 | Astrazeneca Ab | Compounds |
| PL370989A1 (en) | 2001-12-21 | 2005-06-13 | Novo Nordisk A/S | Amide derivatives as gk activators |
| DE60319714T2 (de) | 2002-06-19 | 2009-04-02 | Schering Corp. | Agonisten des cannabinoidrezeptors |
| AU2003243921B2 (en) | 2002-06-27 | 2009-05-07 | Novo Nordisk A/S | Aryl carbonyl derivatives as therapeutic agents |
| DE60336850D1 (en) * | 2003-01-06 | 2011-06-01 | Lilly Co Eli | Substituierte arylcyclopropylacetamide als glucokinaseaktivatoren |
| EP1663113A4 (en) | 2003-09-18 | 2007-06-13 | Merck & Co Inc | SUBSTITUTED SULFONAMIDE |
| JP2007507529A (ja) | 2003-09-30 | 2007-03-29 | サイオス・インコーポレーテツド | 複素環式アミドおよびスルホンアミド |
| CA2567692A1 (en) | 2004-06-08 | 2005-12-29 | Primegen Biotech Llc | Therapeutic reprogramming, hybrid stem cells and maturation |
| JP2006025403A (ja) * | 2004-06-08 | 2006-01-26 | Ricoh Co Ltd | 画像読取装置及び画像形成装置 |
| US20080026987A1 (en) | 2004-06-17 | 2008-01-31 | Novo Nordisk A/S | Use of Liver-Selective Glucokinase Activators |
| SE0401653D0 (sv) * | 2004-06-24 | 2004-06-24 | Astrazeneca Ab | New compounds |
| GB0423043D0 (en) | 2004-10-16 | 2004-11-17 | Astrazeneca Ab | Compounds |
| CN101371585B (zh) * | 2006-01-09 | 2014-07-30 | 汤姆森特许公司 | 提供用于多视图视频编码的提供降低分辨率的更新模式的方法和装置 |
| TWI385161B (zh) * | 2006-02-02 | 2013-02-11 | Mitsubishi Tanabe Pharma Corp | 含氮雜雙環化合物 |
| JP5099814B2 (ja) | 2006-02-02 | 2012-12-19 | 田辺三菱製薬株式会社 | 含窒素複素二環式化合物 |
| DE602007009807D1 (de) | 2006-03-06 | 2010-11-25 | Raqualia Pharma Inc | Sulfonylbenzimidazolderivate |
| RU2008148962A (ru) | 2006-05-12 | 2010-06-20 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Избирательно действующие ингибиторы rоск протеинкиназы и их применение |
| CA2657247A1 (en) * | 2006-07-28 | 2008-01-31 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
-
2008
- 2008-02-25 CA CA002679185A patent/CA2679185A1/en not_active Abandoned
- 2008-02-25 CN CN2008800064275A patent/CN101622231B/zh not_active Expired - Fee Related
- 2008-02-25 EP EP08738368A patent/EP2125735B1/en active Active
- 2008-02-25 US US12/528,770 patent/US8940900B2/en active Active
- 2008-02-25 WO PCT/IN2008/000109 patent/WO2008104994A2/en not_active Ceased
- 2008-02-25 JP JP2009551312A patent/JP5491871B2/ja not_active Expired - Fee Related
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