ES2567753T3 - Derivados de 1,2,4-tiazolidin-3-ona y su uso en el tratamiento del cáncer - Google Patents
Derivados de 1,2,4-tiazolidin-3-ona y su uso en el tratamiento del cáncer Download PDFInfo
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- ES2567753T3 ES2567753T3 ES10759940.9T ES10759940T ES2567753T3 ES 2567753 T3 ES2567753 T3 ES 2567753T3 ES 10759940 T ES10759940 T ES 10759940T ES 2567753 T3 ES2567753 T3 ES 2567753T3
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- methyl
- thiadiazol
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- compound
- oxo
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- 206010028980 Neoplasm Diseases 0.000 title claims description 93
- 201000011510 cancer Diseases 0.000 title claims description 74
- 238000011282 treatment Methods 0.000 title claims description 51
- 150000001875 compounds Chemical class 0.000 claims abstract description 288
- 125000003118 aryl group Chemical group 0.000 claims abstract description 68
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 61
- 150000002367 halogens Chemical class 0.000 claims abstract description 60
- 125000001424 substituent group Chemical group 0.000 claims abstract description 40
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 38
- 125000005843 halogen group Chemical group 0.000 claims abstract description 31
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 23
- 125000006574 non-aromatic ring group Chemical group 0.000 claims abstract description 21
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 18
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 12
- 125000004429 atom Chemical group 0.000 claims abstract description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims description 67
- 239000012453 solvate Substances 0.000 claims description 55
- -1 (4-chlorophenyl) - Chemical class 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 43
- 239000003814 drug Substances 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 229940124597 therapeutic agent Drugs 0.000 claims description 23
- 230000000694 effects Effects 0.000 claims description 19
- 208000026310 Breast neoplasm Diseases 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 239000013066 combination product Substances 0.000 claims description 12
- 229940127555 combination product Drugs 0.000 claims description 12
- 239000012190 activator Substances 0.000 claims description 11
- 239000002671 adjuvant Substances 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 11
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 206010060862 Prostate cancer Diseases 0.000 claims description 6
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- 210000000481 breast Anatomy 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 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 description 4
- HXIOAMUSVHJFJR-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)imino-4-(2-phenoxyethyl)-1,2,4-thiadiazolidin-3-one Chemical compound C1=C(Cl)C(Cl)=CC=C1N=C1N(CCOC=2C=CC=CC=2)C(=O)NS1 HXIOAMUSVHJFJR-UHFFFAOYSA-N 0.000 claims description 4
- AZQPOQDQXYPOTD-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)imino-4-[[3-(trifluoromethyl)phenyl]methyl]-1,2,4-thiadiazolidin-3-one Chemical compound FC(F)(F)C1=CC=CC(CN2C(SNC2=O)=NC=2C=C(Cl)C(Cl)=CC=2)=C1 AZQPOQDQXYPOTD-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
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- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- TZSKWUDSKVQLKM-UHFFFAOYSA-N 3,4-dichloro-n-[4-[(4-fluorophenyl)methyl]-3-oxo-1,2,4-thiadiazolidin-5-ylidene]benzamide Chemical compound C1=CC(F)=CC=C1CN(C(=O)NS1)C1=NC(=O)C1=CC=C(Cl)C(Cl)=C1 TZSKWUDSKVQLKM-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- GWQZFXMHKONFOA-UHFFFAOYSA-N 4-[(3,4-difluorophenyl)methyl]-5-[4-(trifluoromethoxy)phenyl]imino-1,2,4-thiadiazolidin-3-one Chemical compound C1=C(F)C(F)=CC=C1CN(C(=O)NS1)C1=NC1=CC=C(OC(F)(F)F)C=C1 GWQZFXMHKONFOA-UHFFFAOYSA-N 0.000 claims description 3
- HHEABDHDGHECTF-UHFFFAOYSA-N 4-[(3,4-difluorophenyl)methyl]-5-[4-(trifluoromethyl)phenyl]imino-1,2,4-thiadiazolidin-3-one Chemical compound C1=C(F)C(F)=CC=C1CN(C(=O)NS1)C1=NC1=CC=C(C(F)(F)F)C=C1 HHEABDHDGHECTF-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- DYDVLDVRIPKMEL-UHFFFAOYSA-N 4-chloro-n-[4-[(4-chlorophenyl)methyl]-3-oxo-1,2,4-thiadiazolidin-5-ylidene]benzamide Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NS1)C1=NC(=O)C1=CC=C(Cl)C=C1 DYDVLDVRIPKMEL-UHFFFAOYSA-N 0.000 claims description 3
- BYJQGCOTNVMBEJ-UHFFFAOYSA-N 4-chloro-n-[4-[(4-fluorophenyl)methyl]-3-oxo-1,2,4-thiadiazolidin-5-ylidene]benzamide Chemical compound C1=CC(F)=CC=C1CN(C(=O)NS1)C1=NC(=O)C1=CC=C(Cl)C=C1 BYJQGCOTNVMBEJ-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- CTESJDQKVOEUOY-UHFFFAOYSA-N 4-hydroxy-3-[4-(2-hydroxyphenyl)phenyl]-6-oxo-7H-thieno[2,3-b]pyridine-5-carbonitrile Chemical compound OC1=CC=CC=C1C1=CC=C(C=2C=3C(O)=C(C#N)C(=O)NC=3SC=2)C=C1 CTESJDQKVOEUOY-UHFFFAOYSA-N 0.000 claims description 3
- LYSHPGVDISUMCS-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)imino-4-[(3,4-difluorophenyl)methyl]-1,2,4-thiadiazolidin-3-one Chemical compound C1=C(F)C(F)=CC=C1CN(C(=O)NS1)C1=NC1=CC=C(Cl)C(Cl)=C1 LYSHPGVDISUMCS-UHFFFAOYSA-N 0.000 claims description 3
- AJVQFHMIZQIECE-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)imino-4-[(3-fluorophenyl)methyl]-1,2,4-thiadiazolidin-3-one Chemical compound FC1=CC=CC(CN2C(SNC2=O)=NC=2C=C(Cl)C(Cl)=CC=2)=C1 AJVQFHMIZQIECE-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/433—Thidiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Hematology (AREA)
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- Endocrinology (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21373509P | 2009-07-08 | 2009-07-08 | |
| US213735P | 2009-07-08 | ||
| PCT/GB2010/001315 WO2011004162A2 (en) | 2009-07-08 | 2010-07-08 | Compounds useful as medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2567753T3 true ES2567753T3 (es) | 2016-04-26 |
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| MX (1) | MX337516B (enExample) |
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| RS (1) | RS54718B1 (enExample) |
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| 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 |
| US10774064B2 (en) | 2016-06-02 | 2020-09-15 | Cadent Therapeutics, Inc. | Potassium channel modulators |
| ES2908801T3 (es) | 2016-06-07 | 2022-05-04 | Jacobio Pharmaceuticals Co Ltd | Nuevos derivados heterocíclicos útiles como inhibidores de SHP2 |
| HRP20220079T1 (hr) | 2017-01-23 | 2022-04-15 | Cadent Therapeutics, Inc. | Modulatori kalijevih kanala |
| DK3601239T3 (da) | 2017-03-23 | 2024-09-30 | Jacobio Pharmaceuticals Co Ltd | Novel heterocyclic derivatives useful as shp2 inhibitors |
| 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 |
| CA3116339A1 (en) | 2018-10-22 | 2020-04-30 | 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 |
| GB201910092D0 (en) | 2019-07-15 | 2019-08-28 | Balticgruppen Bio Ab | New formulations |
| GB201910093D0 (en) | 2019-07-15 | 2019-08-28 | Balticgruppen Bio Ab | New formulations |
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| 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 |
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| WO2025017193A1 (en) | 2023-07-20 | 2025-01-23 | Betagenon Ab | Methods of treating cardiomyopathy induced by metabolic inflexibility |
| WO2025017194A1 (en) | 2023-07-20 | 2025-01-23 | Betagenon Ab | Methods for regulating blood glucose levels using a dual ampk activator and mitochondrial uncoupler |
| 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 |
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| US4093624A (en) | 1977-01-31 | 1978-06-06 | Icn Pharmaceuticals, Inc. | 1,2,4-Thiadiazolidine-3,5-dione |
| CZ296087B6 (cs) | 2000-05-11 | 2006-01-11 | Consejo Superior Investigaciones Cientificas | Farmaceutický prostredek pro lécbu nemoci, na nízse podílí heterocyklické inhibitory glykogensyntázakinázy GSK-3 |
| 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 |
| WO2006045581A1 (en) * | 2004-10-21 | 2006-05-04 | Neuropharma, S.A. | The use of 1, 2, 4-thiadiazolidine-3, 5-diones as ppar activators |
| EA200800303A1 (ru) | 2005-07-21 | 2008-10-30 | Бетагенон Аб | Применение производных и аналогов тиазола при нарушениях, вызванных свободными жирными кислотами |
| 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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2010
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