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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| EP2081905B1 (en) | 2006-07-28 | 2012-09-12 | Boehringer Ingelheim International GmbH | Sulfonyl compounds which modulate the cb2 receptor |
| CA2664310A1 (en) | 2006-09-25 | 2008-04-03 | 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 |
| US8501955B2 (en) * | 2007-10-08 | 2013-08-06 | Advinus Therapeutics Private Limited | Acetamide derivatives as glucokinase activators, their process and medicinal application |
| JP5492092B2 (ja) | 2007-11-07 | 2014-05-14 | 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受容体を調節する化合物 |
| EP2326629B1 (en) | 2008-07-10 | 2013-10-02 | Boehringer Ingelheim International GmbH | Sulfone compounds which modulate the cb2 receptor |
| WO2010036630A2 (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 |
| JP2013505295A (ja) | 2009-09-22 | 2013-02-14 | 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受容体を選択的に調節する化合物 |
| WO2011080755A1 (en) | 2009-12-29 | 2011-07-07 | Advinus Therapeutics Private Limited | Fused nitrogen heterocyclic compounds, process of preparation and uses thereof |
| US9315454B2 (en) | 2010-01-15 | 2016-04-19 | 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 |
| EP2542539B1 (en) | 2010-03-05 | 2014-02-26 | Boehringer Ingelheim International GmbH | Tetrazole compounds which selectively modulate the cb2 receptor |
| CA2800498C (en) | 2010-03-31 | 2021-11-16 | The Scripps Research Institute | Reprogramming cells |
| WO2011157827A1 (de) | 2010-06-18 | 2011-12-22 | 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 |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| 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 |
| JP5746764B2 (ja) | 2010-07-22 | 2015-07-08 | 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受容体を調節する化合物 |
| WO2012020357A1 (en) * | 2010-08-09 | 2012-02-16 | Advinus Therapeutics Ltd. | Acetamide compounds, their process and pharmaceutical application |
| US9169295B2 (en) * | 2010-10-13 | 2015-10-27 | Bristol-Myers Squibb Company | 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 |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | 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 |
| DK3054936T5 (da) | 2013-10-10 | 2024-03-18 | Eastern Virginia Medical School | 4-((2-hydroxy-3-methoxybenzyl)amino) benzensulfonamid derivater som 12-lipoxygenase inhibitorer |
| WO2016172496A1 (en) | 2015-04-23 | 2016-10-27 | Constellation Pharmaceuticals, Inc. | Lsd1 inhibitors and uses thereof |
| US10647689B2 (en) | 2015-04-28 | 2020-05-12 | Sanford Burnham Prebys Medical Discovery Institute | Apelin receptor agonists and methods of use thereof |
| AU2017275657B2 (en) | 2016-06-02 | 2021-08-19 | Novartis Ag | Potassium channel modulators |
| DK3532459T3 (da) | 2016-10-26 | 2023-10-30 | Constellation Pharmaceuticals Inc | Lsd1-hæmmere og medicinske anvendelser deraf |
| PL3571193T3 (pl) | 2017-01-23 | 2022-04-25 | Cadent Therapeutics, Inc. | Modulatory kanału potasowego |
| SG11202000230VA (en) | 2017-07-11 | 2020-02-27 | Vertex Pharma | Carboxamides as modulators of sodium channels |
| EP3870291A1 (en) | 2018-10-22 | 2021-09-01 | Cadent Therapeutics, Inc. | Crystalline forms of potassium channel modulators |
| US12441703B2 (en) | 2019-01-10 | 2025-10-14 | Vertex Pharmaceuticals Incorporated | Carboxamides as modulators of sodium channels |
| WO2020146612A1 (en) | 2019-01-10 | 2020-07-16 | Vertex Pharmaceuticals Incorporated | Esters and carbamates as modulators of sodium channels |
| CA3189027A1 (en) | 2020-07-11 | 2022-01-20 | Pfizer Inc. | Antiviral heteroaryl ketone derivatives |
| 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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| 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 |
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| 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 | |
| US5792109A (en) | 1994-09-01 | 1998-08-11 | Leland L. Ladd | Irrigation pump and system |
| SI1169312T1 (en) | 1999-03-29 | 2005-02-28 | F. Hoffmann-La Roche Ag | Glucokinase activators |
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| DE60040676D1 (de) | 1999-09-17 | 2008-12-11 | Millennium Pharm Inc | BENZAMIDE UND ÄHNLICHE INHIBITOREN VON FAKTOR Xa |
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| US6353111B1 (en) | 1999-12-15 | 2002-03-05 | Hoffmann-La Roche Inc. | Trans olefinic glucokinase activators |
| KR100502033B1 (ko) | 2000-05-03 | 2005-07-25 | 에프. 호프만-라 로슈 아게 | 알키닐 페닐 헤테로방향족 글루코키나제 활성제 |
| AU778036B2 (en) | 2000-05-08 | 2004-11-11 | F. Hoffmann-La Roche Ag | Substituted phenylacetamides and their use as glucokinase activators |
| KR100519826B1 (ko) | 2000-05-08 | 2005-10-06 | 에프. 호프만-라 로슈 아게 | 파라-아민 치환된 페닐아미드 글루코키나제 활성화제 |
| MXPA03000365A (es) | 2000-07-20 | 2003-05-27 | Hoffmann La Roche | Bencenacetamida substituida con alfa-acilo y alfa-heteroatomo como activadores de la glucocinasa. |
| US7067539B2 (en) | 2001-02-08 | 2006-06-27 | Schering Corporation | Cannabinoid receptor ligands |
| SE0102764D0 (sv) * | 2001-08-17 | 2001-08-17 | Astrazeneca Ab | Compounds |
| WO2003055482A1 (en) | 2001-12-21 | 2003-07-10 | Novo Nordisk A/S | Amide derivatives as gk activators |
| MXPA04012704A (es) | 2002-06-19 | 2005-03-23 | Schering Corp | Agonistas de los receptores canabinoides. |
| BR0312023A (pt) | 2002-06-27 | 2005-03-22 | Novo Nordisk As | Composto, composto ativador da glicose cinase, método para evitar a hipoglicemia, uso de um composto, e, composição farmacêutica |
| DE60336850D1 (en) | 2003-01-06 | 2011-06-01 | Lilly Co Eli | Substituierte arylcyclopropylacetamide als glucokinaseaktivatoren |
| CA2538291A1 (en) | 2003-09-18 | 2005-03-31 | Merck & Co., Inc. | Substituted sulfonamides |
| EP1675830A4 (en) * | 2003-09-30 | 2008-08-20 | Scios Inc | HETEROCYCLIC AMIDES AND SULFONAMIDES |
| 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 |
| EP1758989A2 (en) | 2004-06-08 | 2007-03-07 | PrimeGen Biotech LLC | Therapeutic reprogramming, hybrid stem cells and maturation |
| JP2008502658A (ja) * | 2004-06-17 | 2008-01-31 | ノボ ノルディスク アクティーゼルスカブ | 肝臓選択的グルコキナーゼ活性化因子の使用 |
| SE0401653D0 (sv) * | 2004-06-24 | 2004-06-24 | Astrazeneca Ab | New compounds |
| GB0423043D0 (en) | 2004-10-16 | 2004-11-17 | Astrazeneca Ab | Compounds |
| JP5535485B2 (ja) * | 2006-01-09 | 2014-07-02 | トムソン ライセンシング | 削減された分解能更新モードをマルチビュー・ビデオ符号化に提供する方法及び装置 |
| 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 |
| TWI385161B (zh) * | 2006-02-02 | 2013-02-11 | Mitsubishi Tanabe Pharma Corp | 含氮雜雙環化合物 |
| EP1994011B1 (en) | 2006-03-06 | 2010-10-13 | RaQualia Pharma Inc | Sulfonyl benzimidazole derivatives |
| ATE478865T1 (de) | 2006-05-12 | 2010-09-15 | Vertex Pharma | Selektive rock-proteinkinasehemmer und ihre verwendung |
| EP2081905B1 (en) | 2006-07-28 | 2012-09-12 | Boehringer Ingelheim International GmbH | Sulfonyl compounds which modulate the cb2 receptor |
-
2008
- 2008-02-25 JP JP2009551312A patent/JP5491871B2/ja not_active Expired - Fee Related
- 2008-02-25 WO PCT/IN2008/000109 patent/WO2008104994A2/en not_active Ceased
- 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 CA CA002679185A patent/CA2679185A1/en not_active Abandoned
- 2008-02-25 US US12/528,770 patent/US8940900B2/en active Active
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