JP2012532854A5 - - Google Patents
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- JP2012532854A5 JP2012532854A5 JP2012519055A JP2012519055A JP2012532854A5 JP 2012532854 A5 JP2012532854 A5 JP 2012532854A5 JP 2012519055 A JP2012519055 A JP 2012519055A JP 2012519055 A JP2012519055 A JP 2012519055A JP 2012532854 A5 JP2012532854 A5 JP 2012532854A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- thiadiazol
- formula
- compound
- oxo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001875 compounds Chemical class 0.000 claims description 52
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 11
- -1 4H- [1,2,4] -triazolyl Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims 27
- 230000000144 pharmacologic effect Effects 0.000 claims 26
- 239000012453 solvate Substances 0.000 claims 25
- 125000003118 aryl group Chemical group 0.000 claims 14
- 206010028980 Neoplasm Diseases 0.000 claims 13
- 201000011510 cancer Diseases 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 239000002671 adjuvant Substances 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims 5
- 239000000047 product Substances 0.000 claims 5
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 239000013066 combination product Substances 0.000 claims 4
- 229940127555 combination product Drugs 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 4
- 229940124597 therapeutic agent Drugs 0.000 claims 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- NOTGFIUVDGNKRI-UUOKFMHZSA-N AICA ribonucleotide Chemical compound NC1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(O)=O)O1 NOTGFIUVDGNKRI-UUOKFMHZSA-N 0.000 claims 2
- 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims 2
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000019691 hematopoietic and lymphoid cell neoplasm Diseases 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- MNULEGDCPYONBU-WMBHJXFZSA-N (1r,4s,5e,5'r,6'r,7e,10s,11r,12s,14r,15s,16s,18r,19s,20r,21e,25s,26r,27s,29s)-4-ethyl-11,12,15,19-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',10,12,14,16,18,20,26,29-nonamethylspiro[24,28-dioxabicyclo[23.3.1]nonacosa-5,7,21-triene-27,2'-oxane]-13,17,23-trio Polymers O([C@@H]1CC[C@@H](/C=C/C=C/C[C@H](C)[C@@H](O)[C@](C)(O)C(=O)[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@H](C)[C@@H](O)[C@H](C)/C=C/C(=O)O[C@H]([C@H]2C)[C@H]1C)CC)[C@]12CC[C@@H](C)[C@@H](C[C@H](C)O)O1 MNULEGDCPYONBU-WMBHJXFZSA-N 0.000 claims 1
- MNULEGDCPYONBU-DJRUDOHVSA-N (1s,4r,5z,5'r,6'r,7e,10s,11r,12s,14r,15s,18r,19r,20s,21e,26r,27s)-4-ethyl-11,12,15,19-tetrahydroxy-6'-(2-hydroxypropyl)-5',10,12,14,16,18,20,26,29-nonamethylspiro[24,28-dioxabicyclo[23.3.1]nonacosa-5,7,21-triene-27,2'-oxane]-13,17,23-trione Polymers O([C@H]1CC[C@H](\C=C/C=C/C[C@H](C)[C@@H](O)[C@](C)(O)C(=O)[C@H](C)[C@@H](O)C(C)C(=O)[C@H](C)[C@H](O)[C@@H](C)/C=C/C(=O)OC([C@H]2C)C1C)CC)[C@]12CC[C@@H](C)[C@@H](CC(C)O)O1 MNULEGDCPYONBU-DJRUDOHVSA-N 0.000 claims 1
- VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 claims 1
- MNULEGDCPYONBU-YNZHUHFTSA-N (4Z,18Z,20Z)-22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethylspiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-oxane]-3,9,13-trione Polymers CC1C(C2C)OC(=O)\C=C/C(C)C(O)C(C)C(=O)C(C)C(O)C(C)C(=O)C(C)(O)C(O)C(C)C\C=C/C=C\C(CC)CCC2OC21CCC(C)C(CC(C)O)O2 MNULEGDCPYONBU-YNZHUHFTSA-N 0.000 claims 1
- MNULEGDCPYONBU-VVXVDZGXSA-N (5e,5'r,7e,10s,11r,12s,14s,15r,16r,18r,19s,20r,21e,26r,29s)-4-ethyl-11,12,15,19-tetrahydroxy-6'-[(2s)-2-hydroxypropyl]-5',10,12,14,16,18,20,26,29-nonamethylspiro[24,28-dioxabicyclo[23.3.1]nonacosa-5,7,21-triene-27,2'-oxane]-13,17,23-trione Polymers C([C@H](C)[C@@H](O)[C@](C)(O)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@H](C)/C=C/C(=O)OC([C@H]1C)[C@H]2C)\C=C\C=C\C(CC)CCC2OC21CC[C@@H](C)C(C[C@H](C)O)O2 MNULEGDCPYONBU-VVXVDZGXSA-N 0.000 claims 1
- 125000001894 2,4,6-trinitrophenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O 0.000 claims 1
- QPEXDGNCMPBSAR-UHFFFAOYSA-N 2,4-dichloro-n-[2-[(4-fluorophenyl)methyl]-3-oxo-1,2,4-thiadiazol-5-yl]benzamide Chemical compound C1=CC(F)=CC=C1CN1C(=O)N=C(NC(=O)C=2C(=CC(Cl)=CC=2)Cl)S1 QPEXDGNCMPBSAR-UHFFFAOYSA-N 0.000 claims 1
- FUXNPGYQRLEJOH-UHFFFAOYSA-N 2,6-dichloro-n-[2-[(4-fluorophenyl)methyl]-3-oxo-1,2,4-thiadiazol-5-yl]benzamide Chemical compound C1=CC(F)=CC=C1CN1C(=O)N=C(NC(=O)C=2C(=CC=CC=2Cl)Cl)S1 FUXNPGYQRLEJOH-UHFFFAOYSA-N 0.000 claims 1
- LKOHEZNWJKGELG-UHFFFAOYSA-N 2-(2-phenylethyl)-5-[4-(trifluoromethoxy)anilino]-1,2,4-thiadiazol-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(S1)=NC(=O)N1CCC1=CC=CC=C1 LKOHEZNWJKGELG-UHFFFAOYSA-N 0.000 claims 1
- HGTKLMBPGLDIFR-UHFFFAOYSA-N 2-(2-phenylethyl)-5-[4-(trifluoromethyl)anilino]-1,2,4-thiadiazol-3-one Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(S1)=NC(=O)N1CCC1=CC=CC=C1 HGTKLMBPGLDIFR-UHFFFAOYSA-N 0.000 claims 1
- GWIUBVYZRHTBHY-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[3-oxo-2-[[3-(trifluoromethyl)phenyl]methyl]-1,2,4-thiadiazol-5-yl]acetamide Chemical compound C1=CC(F)=CC=C1CC(=O)NC(S1)=NC(=O)N1CC1=CC=CC(C(F)(F)F)=C1 GWIUBVYZRHTBHY-UHFFFAOYSA-N 0.000 claims 1
- HNGKUGUJMPSSGY-UHFFFAOYSA-N 2-[(3,4-difluorophenyl)methyl]-5-[4-(trifluoromethoxy)anilino]-1,2,4-thiadiazol-3-one Chemical compound C1=C(F)C(F)=CC=C1CN1C(=O)N=C(NC=2C=CC(OC(F)(F)F)=CC=2)S1 HNGKUGUJMPSSGY-UHFFFAOYSA-N 0.000 claims 1
- XJTWKJIKTOVTGK-UHFFFAOYSA-N 2-[(3,4-difluorophenyl)methyl]-5-[4-(trifluoromethyl)anilino]-1,2,4-thiadiazol-3-one Chemical compound C1=C(F)C(F)=CC=C1CN1C(=O)N=C(NC=2C=CC(=CC=2)C(F)(F)F)S1 XJTWKJIKTOVTGK-UHFFFAOYSA-N 0.000 claims 1
- RJZSSMHOEKAAPX-UHFFFAOYSA-N 2-[(3-fluorophenyl)methyl]-5-[4-(trifluoromethoxy)anilino]-1,2,4-thiadiazol-3-one Chemical compound FC1=CC=CC(CN2C(N=C(NC=3C=CC(OC(F)(F)F)=CC=3)S2)=O)=C1 RJZSSMHOEKAAPX-UHFFFAOYSA-N 0.000 claims 1
- LZADXQXNWDOMDY-UHFFFAOYSA-N 2-[(3-fluorophenyl)methyl]-5-[4-(trifluoromethyl)anilino]-1,2,4-thiadiazol-3-one Chemical compound FC1=CC=CC(CN2C(N=C(NC=3C=CC(=CC=3)C(F)(F)F)S2)=O)=C1 LZADXQXNWDOMDY-UHFFFAOYSA-N 0.000 claims 1
- AMUWSZXTELUHFX-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-5-[4-(trifluoromethoxy)anilino]-1,2,4-thiadiazol-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(S1)=NC(=O)N1CC1=CC=C(Cl)C=C1 AMUWSZXTELUHFX-UHFFFAOYSA-N 0.000 claims 1
- ZNNXRHUTYUXTHC-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-5-[4-(trifluoromethyl)anilino]-1,2,4-thiadiazol-3-one Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(S1)=NC(=O)N1CC1=CC=C(Cl)C=C1 ZNNXRHUTYUXTHC-UHFFFAOYSA-N 0.000 claims 1
- RFZWGFCULXKUMF-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methyl]-5-[4-(trifluoromethoxy)anilino]-1,2,4-thiadiazol-3-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N=C(NC=2C=CC(OC(F)(F)F)=CC=2)S1 RFZWGFCULXKUMF-UHFFFAOYSA-N 0.000 claims 1
- WYBNVXBKQQMPFJ-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methyl]-5-[4-(trifluoromethyl)anilino]-1,2,4-thiadiazol-3-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N=C(NC=2C=CC(=CC=2)C(F)(F)F)S1 WYBNVXBKQQMPFJ-UHFFFAOYSA-N 0.000 claims 1
- NHYKNGYFZCJBDR-UHFFFAOYSA-N 2-[2-(4-chloro-n-methylanilino)ethyl]-5-(3,4-dichloroanilino)-1,2,4-thiadiazol-3-one Chemical compound C=1C=C(Cl)C=CC=1N(C)CCN(C(N=1)=O)SC=1NC1=CC=C(Cl)C(Cl)=C1 NHYKNGYFZCJBDR-UHFFFAOYSA-N 0.000 claims 1
- UQVPZZXWWFWQNN-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)sulfanylethyl]-5-(3,4-dichloroanilino)-1,2,4-thiadiazol-3-one Chemical compound C1=CC(Cl)=CC=C1SCCN1C(=O)N=C(NC=2C=C(Cl)C(Cl)=CC=2)S1 UQVPZZXWWFWQNN-UHFFFAOYSA-N 0.000 claims 1
- YPPMKZRGLLMSDM-UHFFFAOYSA-N 2-chloro-6-fluoro-n-[2-[(4-fluorophenyl)methyl]-3-oxo-1,2,4-thiadiazol-5-yl]benzamide Chemical compound C1=CC(F)=CC=C1CN1C(=O)N=C(NC(=O)C=2C(=CC=CC=2F)Cl)S1 YPPMKZRGLLMSDM-UHFFFAOYSA-N 0.000 claims 1
- FSHRXYMLLSKYGV-UHFFFAOYSA-N 3,4-dichloro-n-[2-[(4-fluorophenyl)methyl]-3-oxo-1,2,4-thiadiazol-5-yl]benzamide Chemical compound C1=CC(F)=CC=C1CN1C(=O)N=C(NC(=O)C=2C=C(Cl)C(Cl)=CC=2)S1 FSHRXYMLLSKYGV-UHFFFAOYSA-N 0.000 claims 1
- NDEIURVSGKHEAW-UHFFFAOYSA-N 3,4-dichloro-n-[2-[1-(4-fluorophenyl)cyclopropyl]-3-oxo-1,2,4-thiadiazol-5-yl]benzamide Chemical compound C1=CC(F)=CC=C1C1(N2C(N=C(NC(=O)C=3C=C(Cl)C(Cl)=CC=3)S2)=O)CC1 NDEIURVSGKHEAW-UHFFFAOYSA-N 0.000 claims 1
- HWOJETIWOGVVBU-UHFFFAOYSA-N 3,4-difluoro-n-[2-[(4-fluorophenyl)methyl]-3-oxo-1,2,4-thiadiazol-5-yl]benzamide Chemical compound C1=CC(F)=CC=C1CN1C(=O)N=C(NC(=O)C=2C=C(F)C(F)=CC=2)S1 HWOJETIWOGVVBU-UHFFFAOYSA-N 0.000 claims 1
- FMPOTICVEOAYQK-UHFFFAOYSA-N 3,5-difluoro-n-[2-[(4-fluorophenyl)methyl]-3-oxo-1,2,4-thiadiazol-5-yl]benzamide Chemical compound C1=CC(F)=CC=C1CN1C(=O)N=C(NC(=O)C=2C=C(F)C=C(F)C=2)S1 FMPOTICVEOAYQK-UHFFFAOYSA-N 0.000 claims 1
- UMWQWADVYZQVBY-UHFFFAOYSA-N 3-[[5-(4-chloroanilino)-3-oxo-1,2,4-thiadiazol-2-yl]methyl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(CN2C(N=C(NC=3C=CC(Cl)=CC=3)S2)=O)=C1 UMWQWADVYZQVBY-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- DEIHGKFXCGHEGK-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]-5-(3,4-dichlorophenyl)imino-1,2,4-thiadiazolidin-3-one Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NS1)C1=NC1=CC=C(Cl)C(Cl)=C1 DEIHGKFXCGHEGK-UHFFFAOYSA-N 0.000 claims 1
- QGGKZABFKBNKLA-UHFFFAOYSA-N 4-[1-(4-chlorophenyl)cyclopropyl]-5-(4-chlorophenyl)imino-1,2,4-thiadiazolidin-3-one Chemical compound C1=CC(Cl)=CC=C1N=C1N(C2(CC2)C=2C=CC(Cl)=CC=2)C(=O)NS1 QGGKZABFKBNKLA-UHFFFAOYSA-N 0.000 claims 1
- PESMVTAMUPTUQX-UHFFFAOYSA-N 4-[2-(4-chloro-N-methylanilino)ethyl]-5-(3,4-dichlorophenyl)-1-imino-1,2,4-thiadiazolidin-3-one Chemical compound ClC1=CC=C(C=C1)N(CCN1C(NS(C1C1=CC(=C(C=C1)Cl)Cl)=N)=O)C PESMVTAMUPTUQX-UHFFFAOYSA-N 0.000 claims 1
- LVDORRLYOXNORK-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)sulfanylethyl]-5-(3,4-dichlorophenyl)imino-1,2,4-thiadiazolidin-3-one Chemical compound C1=CC(Cl)=CC=C1SCCN(C(=O)NS1)C1=NC1=CC=C(Cl)C(Cl)=C1 LVDORRLYOXNORK-UHFFFAOYSA-N 0.000 claims 1
- OQCAQPYSSFQACS-UHFFFAOYSA-N 4-[[2-[(3,4-difluorophenyl)methyl]-3-oxo-1,2,4-thiadiazol-5-yl]amino]benzonitrile Chemical compound C1=C(F)C(F)=CC=C1CN1C(=O)N=C(NC=2C=CC(=CC=2)C#N)S1 OQCAQPYSSFQACS-UHFFFAOYSA-N 0.000 claims 1
- XKILBXRPFVVUBB-UHFFFAOYSA-N 4-[[4-[(3,4-difluorophenyl)methyl]-3-oxo-1,2,4-thiadiazolidin-5-ylidene]amino]benzonitrile Chemical compound C1=C(F)C(F)=CC=C1CN(C(=O)NS1)C1=NC1=CC=C(C#N)C=C1 XKILBXRPFVVUBB-UHFFFAOYSA-N 0.000 claims 1
- HYYOUTIDAKSXEU-UHFFFAOYSA-N 4-benzhydryl-5-(3,4-dichlorophenyl)imino-1,2,4-thiadiazolidin-3-one Chemical compound C1=C(Cl)C(Cl)=CC=C1N=C1N(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C(=O)NS1 HYYOUTIDAKSXEU-UHFFFAOYSA-N 0.000 claims 1
- KVQYNKBQULGFLP-UHFFFAOYSA-N 4-chloro-n-[2-[(3,4-difluorophenyl)methyl]-3-oxo-1,2,4-thiadiazol-5-yl]benzamide Chemical compound C1=C(F)C(F)=CC=C1CN1C(=O)N=C(NC(=O)C=2C=CC(Cl)=CC=2)S1 KVQYNKBQULGFLP-UHFFFAOYSA-N 0.000 claims 1
- WEDWLYRQKUTOAX-UHFFFAOYSA-N 4-chloro-n-[2-[(4-chlorophenyl)methyl]-3-oxo-1,2,4-thiadiazol-5-yl]benzamide Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)N=C(NC(=O)C=2C=CC(Cl)=CC=2)S1 WEDWLYRQKUTOAX-UHFFFAOYSA-N 0.000 claims 1
- WWKBAXKETBKLRJ-UHFFFAOYSA-N 4-chloro-n-[2-[(4-fluorophenyl)methyl]-3-oxo-1,2,4-thiadiazol-5-yl]benzamide Chemical compound C1=CC(F)=CC=C1CN1C(=O)N=C(NC(=O)C=2C=CC(Cl)=CC=2)S1 WWKBAXKETBKLRJ-UHFFFAOYSA-N 0.000 claims 1
- ZUHLQVQSIGNCJR-UHFFFAOYSA-N 4-chloro-n-[2-[2-(4-chlorophenyl)sulfanylethyl]-3-oxo-1,2,4-thiadiazol-5-yl]benzamide Chemical compound C1=CC(Cl)=CC=C1SCCN1C(=O)N=C(NC(=O)C=2C=CC(Cl)=CC=2)S1 ZUHLQVQSIGNCJR-UHFFFAOYSA-N 0.000 claims 1
- VFZXNINYXOCKCV-UHFFFAOYSA-N 4-chloro-n-[3-oxo-4-[[3-(trifluoromethyl)phenyl]methyl]-1,2,4-thiadiazolidin-5-ylidene]benzamide Chemical compound FC(F)(F)C1=CC=CC(CN2C(SNC2=O)=NC(=O)C=2C=CC(Cl)=CC=2)=C1 VFZXNINYXOCKCV-UHFFFAOYSA-N 0.000 claims 1
- MNULEGDCPYONBU-UHFFFAOYSA-N 4-ethyl-11,12,15,19-tetrahydroxy-6'-(2-hydroxypropyl)-5',10,12,14,16,18,20,26,29-nonamethylspiro[24,28-dioxabicyclo[23.3.1]nonacosa-5,7,21-triene-27,2'-oxane]-13,17,23-trione Polymers CC1C(C2C)OC(=O)C=CC(C)C(O)C(C)C(=O)C(C)C(O)C(C)C(=O)C(C)(O)C(O)C(C)CC=CC=CC(CC)CCC2OC21CCC(C)C(CC(C)O)O2 MNULEGDCPYONBU-UHFFFAOYSA-N 0.000 claims 1
- IHAHDANKRDSQDI-UHFFFAOYSA-N 4-fluoro-n-[3-oxo-2-[[3-(trifluoromethyl)phenyl]methyl]-1,2,4-thiadiazol-5-yl]benzamide Chemical compound C1=CC(F)=CC=C1C(=O)NC(S1)=NC(=O)N1CC1=CC=CC(C(F)(F)F)=C1 IHAHDANKRDSQDI-UHFFFAOYSA-N 0.000 claims 1
- CQPHWPNJPUDZJN-UHFFFAOYSA-N 5-(3,4-dichloroanilino)-2-(2-phenoxyethyl)-1,2,4-thiadiazol-3-one Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(S1)=NC(=O)N1CCOC1=CC=CC=C1 CQPHWPNJPUDZJN-UHFFFAOYSA-N 0.000 claims 1
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Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100931145B1 (ko) * | 2008-07-04 | 2009-12-10 | 현대자동차주식회사 | 조정식 킥 다운 스위치의 조작기구 |
| WO2013108026A1 (en) | 2012-01-17 | 2013-07-25 | Baltic Bio Ab | Thiadiazolone derivatives useful in the treatment of diabetes |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| CA2905242C (en) | 2013-03-15 | 2016-11-29 | Pfizer Inc. | Indole compounds that activate ampk |
| GB201308325D0 (en) * | 2013-05-09 | 2013-06-19 | Immodulon Therapeutics Ltd | Cancer Therapy |
| AU2017275657B2 (en) | 2016-06-02 | 2021-08-19 | Novartis Ag | Potassium channel modulators |
| HUE057838T2 (hu) | 2016-06-07 | 2022-06-28 | Jacobio Pharmaceuticals Co Ltd | SHP2 inhibitorokként hasznos új heterociklusos származékok |
| EP3571193B1 (en) | 2017-01-23 | 2021-12-01 | Cadent Therapeutics, Inc. | Potassium channel modulators |
| TWI664175B (zh) | 2017-03-23 | 2019-07-01 | 大陸商北京加科思新藥研發有限公司 | 用於作為shp2抑制劑之新穎雜環衍生物 |
| CN112839935A (zh) | 2018-09-26 | 2021-05-25 | 北京加科思新药研发有限公司 | 可用作shp2抑制剂的新型杂环衍生物 |
| EP3870291A1 (en) | 2018-10-22 | 2021-09-01 | Cadent Therapeutics, Inc. | Crystalline forms of potassium channel modulators |
| WO2020095010A1 (en) * | 2018-11-05 | 2020-05-14 | Balticgruppen Bio Ab | Methods of treating diabetes in severe insulin-resistant diabetic subjects |
| CN109879808B (zh) * | 2019-03-05 | 2020-10-16 | 北京工业大学 | 一种含五元唑类杂环基查尔酮类衍生物及制备方法和医药用途 |
| GB201910093D0 (en) | 2019-07-15 | 2019-08-28 | Balticgruppen Bio Ab | New formulations |
| GB201910092D0 (en) | 2019-07-15 | 2019-08-28 | Balticgruppen Bio Ab | New formulations |
| US11691954B2 (en) | 2019-10-18 | 2023-07-04 | Betagenon Ab | Formulations |
| GB201915094D0 (en) * | 2019-10-18 | 2019-12-04 | Balticgruppen Bio Ab | New formulations |
| GB202015585D0 (en) * | 2020-10-01 | 2020-11-18 | Betagenon Bio Ab | New compounds |
| GB202100352D0 (en) * | 2021-01-12 | 2021-02-24 | Balticgruppen Bio Ab | New methods |
| GB202112529D0 (en) | 2021-09-02 | 2021-10-20 | Betagenon Bio Ab | New compounds |
| WO2025017194A1 (en) | 2023-07-20 | 2025-01-23 | Betagenon Ab | Methods for regulating blood glucose levels using a dual ampk activator and mitochondrial uncoupler |
| WO2025017193A1 (en) | 2023-07-20 | 2025-01-23 | Betagenon Ab | Methods of treating cardiomyopathy induced by metabolic inflexibility |
| WO2025027205A1 (en) | 2023-08-03 | 2025-02-06 | Betagenon Ab | Treatment of cancer with the pdk inhibitor 4-chloro-n-(2-(4-chlorobenzyl)-3-oxo-2,3-dihydro-1,2,4-thiadiazol-5-yl)benzamide |
| WO2025252672A1 (en) | 2024-06-03 | 2025-12-11 | Betagenon Ab | Use of tryptophan and metabolites thereof as biomarkers for treatment methods |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4093624A (en) | 1977-01-31 | 1978-06-06 | Icn Pharmaceuticals, Inc. | 1,2,4-Thiadiazolidine-3,5-dione |
| ES2166328B1 (es) * | 2000-05-11 | 2003-09-16 | Consejo Superior Investigacion | Inhibidores heterociclicos del enzima gsk 3 utiles en el tratamiento de procesos neurodegenerativos e hiperproliferativos |
| WO2001085685A1 (en) | 2000-05-11 | 2001-11-15 | Consejo Superior Investigaciones Cientificas | Heterocyclic inhibitors of glycogen synthase kinase gsk-3 |
| WO2006045581A1 (en) * | 2004-10-21 | 2006-05-04 | Neuropharma, S.A. | The use of 1, 2, 4-thiadiazolidine-3, 5-diones as ppar activators |
| EP1906956A2 (en) | 2005-07-21 | 2008-04-09 | Betagenon AB | Use of thiazole derivatives and analogues in disorders caused by free fatty acids |
| WO2008090356A1 (en) * | 2007-01-25 | 2008-07-31 | Betagenon Ab | Thiazolidinone derivatives useful in the treatment of cancer and disorders caused by excess adiposity |
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