JP2009532379A - ＰＴＰａｓｅのチアジアゾリジノン阻害剤 - Google Patents

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Publication number

JP2009532379A

JP2009532379A JP2009503258A JP2009503258A JP2009532379A JP 2009532379 A JP2009532379 A JP 2009532379A JP 2009503258 A JP2009503258 A JP 2009503258A JP 2009503258 A JP2009503258 A JP 2009503258A JP 2009532379 A JP2009532379 A JP 2009532379A

Authority

JP

Japan

Prior art keywords

thiadiazolidin

hydroxy

phenyl

trioxo

substituted

Prior art date

2006-03-31

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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• 239000003112 inhibitor Substances 0.000 title abstract description 19
• UXHCYSLUHBOEGI-UHFFFAOYSA-N 1-(4-bromophenyl)imino-5,6,7,8-tetrahydro-[1,3,4]thiadiazolo[3,4-a]pyridazin-3-one Chemical compound C1=CC(Br)=CC=C1N=C1N2CCCCN2C(=O)S1 UXHCYSLUHBOEGI-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 465
• 238000011282 treatment Methods 0.000 claims abstract description 35
• 230000000694 effects Effects 0.000 claims abstract description 31
• 102000002727 Protein Tyrosine Phosphatase Human genes 0.000 claims abstract description 24
• 108020000494 protein-tyrosine phosphatase Proteins 0.000 claims abstract description 24
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 23
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 20
• 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 18
• 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 17
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 17
• 230000001404 mediated effect Effects 0.000 claims abstract description 15
• 201000010099 disease Diseases 0.000 claims abstract description 13
• 206010020772 Hypertension Diseases 0.000 claims abstract description 12
• 208000017170 Lipid metabolism disease Diseases 0.000 claims abstract description 12
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 11
• 208000002705 Glucose Intolerance Diseases 0.000 claims abstract description 11
• 206010061218 Inflammation Diseases 0.000 claims abstract description 11
• 208000008589 Obesity Diseases 0.000 claims abstract description 11
• 208000001132 Osteoporosis Diseases 0.000 claims abstract description 11
• 206010033645 Pancreatitis Diseases 0.000 claims abstract description 11
• 201000011510 cancer Diseases 0.000 claims abstract description 11
• 210000000987 immune system Anatomy 0.000 claims abstract description 11
• 230000004054 inflammatory process Effects 0.000 claims abstract description 11
• 208000023589 ischemic disease Diseases 0.000 claims abstract description 11
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 11
• 235000020824 obesity Nutrition 0.000 claims abstract description 11
• 208000037803 restenosis Diseases 0.000 claims abstract description 11
• 230000002792 vascular Effects 0.000 claims abstract description 11
• 208000002551 irritable bowel syndrome Diseases 0.000 claims abstract description 10
• 201000009104 prediabetes syndrome Diseases 0.000 claims abstract description 10
• 208000035473 Communicable disease Diseases 0.000 claims abstract description 8
• -1 aralkoxy Chemical group 0.000 claims description 319
• 125000000217 alkyl group Chemical group 0.000 claims description 176
• 150000003839 salts Chemical class 0.000 claims description 133
• 125000003118 aryl group Chemical group 0.000 claims description 112
• 229910052739 hydrogen Inorganic materials 0.000 claims description 100
• 239000001257 hydrogen Substances 0.000 claims description 99
• 125000000623 heterocyclic group Chemical group 0.000 claims description 95
• 238000000034 method Methods 0.000 claims description 85
• 125000003545 alkoxy group Chemical group 0.000 claims description 65
• 125000001072 heteroaryl group Chemical group 0.000 claims description 59
• 150000002431 hydrogen Chemical class 0.000 claims description 58
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 57
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 57
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 56
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 49
• 125000001424 substituent group Chemical group 0.000 claims description 47
• 238000006243 chemical reaction Methods 0.000 claims description 46
• 229910052736 halogen Inorganic materials 0.000 claims description 44
• 150000002367 halogens Chemical class 0.000 claims description 44
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 40
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
• 125000002947 alkylene group Chemical group 0.000 claims description 36
• 150000001721 carbon Chemical group 0.000 claims description 33
• 229910052799 carbon Inorganic materials 0.000 claims description 33
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 32
• 125000004104 aryloxy group Chemical group 0.000 claims description 29
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
• 125000004414 alkyl thio group Chemical group 0.000 claims description 27
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 26
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
• 239000002253 acid Substances 0.000 claims description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims description 25
• 125000002252 acyl group Chemical group 0.000 claims description 24
• 125000004423 acyloxy group Chemical group 0.000 claims description 24
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 24
• 125000001589 carboacyl group Chemical group 0.000 claims description 23
• 229910052760 oxygen Inorganic materials 0.000 claims description 21
• 125000005110 aryl thio group Chemical group 0.000 claims description 20
• 238000004519 manufacturing process Methods 0.000 claims description 19
• 239000001301 oxygen Substances 0.000 claims description 19
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
• 125000004470 heterocyclooxy group Chemical group 0.000 claims description 18
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 17
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 14
• 125000003282 alkyl amino group Chemical group 0.000 claims description 13
• 241000124008 Mammalia Species 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 12
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
• 150000001408 amides Chemical class 0.000 claims description 10
• 239000003472 antidiabetic agent Substances 0.000 claims description 10
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 239000000883 anti-obesity agent Substances 0.000 claims description 8
• 229940125710 antiobesity agent Drugs 0.000 claims description 8
• 229940030600 antihypertensive agent Drugs 0.000 claims description 7
• 239000002220 antihypertensive agent Substances 0.000 claims description 7
• 229940080818 propionamide Drugs 0.000 claims description 7
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 6
• 241001334141 Rugopharynx alpha Species 0.000 claims description 6
• 239000003524 antilipemic agent Substances 0.000 claims description 6
• VAMZMKAHERCOQK-UHFFFAOYSA-N 5-[4-(3-aminopropyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC(CCCN)=CC=C1N1S(=O)(=O)NC(=O)C1 VAMZMKAHERCOQK-UHFFFAOYSA-N 0.000 claims description 5
• 230000003178 anti-diabetic effect Effects 0.000 claims description 5
• 229940125708 antidiabetic agent Drugs 0.000 claims description 5
• 239000008103 glucose Substances 0.000 claims description 5
• 238000006467 substitution reaction Methods 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• HODRTBMLDOAJBU-UHFFFAOYSA-N 2-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanoylamino]-2-methylpropanoic acid Chemical compound OC1=CC(CCC(=O)NC(C)(C)C(O)=O)=CC=C1N1S(=O)(=O)NC(=O)C1 HODRTBMLDOAJBU-UHFFFAOYSA-N 0.000 claims description 4
• JOUMBESLECZHQX-UHFFFAOYSA-N 2-hydroxy-6-[4-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanoylamino]butoxy]benzoic acid Chemical compound OC(=O)C1=C(O)C=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 JOUMBESLECZHQX-UHFFFAOYSA-N 0.000 claims description 4
• UKAXZSKBXYSIHH-UHFFFAOYSA-N 3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-n-methyl-n-propan-2-ylpropanamide Chemical compound OC1=CC(CCC(=O)N(C)C(C)C)=CC=C1N1S(=O)(=O)NC(=O)C1 UKAXZSKBXYSIHH-UHFFFAOYSA-N 0.000 claims description 4
• HMWZVIQLDATKAD-UHFFFAOYSA-N 5-[4-[2-(1-acetylpiperidin-2-yl)ethyl]-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC(=O)N1CCCCC1CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 HMWZVIQLDATKAD-UHFFFAOYSA-N 0.000 claims description 4
• IMXVQUQFQBVMMT-UHFFFAOYSA-N methyl 2-hydroxy-6-[4-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanoylamino]butoxy]benzoate Chemical compound COC(=O)C1=C(O)C=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 IMXVQUQFQBVMMT-UHFFFAOYSA-N 0.000 claims description 4
• CCFNBOVNMOLCHA-UHFFFAOYSA-N n-[4-(2-acetyl-3-hydroxyphenoxy)butyl]-3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanamide Chemical compound CC(=O)C1=C(O)C=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 CCFNBOVNMOLCHA-UHFFFAOYSA-N 0.000 claims description 4
• KISAHPBDCNNXEH-UHFFFAOYSA-N tert-butyl 2-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 KISAHPBDCNNXEH-UHFFFAOYSA-N 0.000 claims description 4
• ACXAIHMIXWKFBX-AWEZNQCLSA-N 2,2,2-trifluoro-n-[(2s)-1-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-3-phenylpropan-2-yl]acetamide Chemical compound C([C@@H](CC=1C=C(C(=CC=1)N1S(NC(=O)C1)(=O)=O)O)NC(=O)C(F)(F)F)C1=CC=CC=C1 ACXAIHMIXWKFBX-AWEZNQCLSA-N 0.000 claims description 3
• ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 3
• SQYAIEZNQYDVGM-UHFFFAOYSA-N 2-hydroxy-6-[4-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanoylamino]butoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=C(O)C=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 SQYAIEZNQYDVGM-UHFFFAOYSA-N 0.000 claims description 3
• MJFXNCSBCSGTCI-UHFFFAOYSA-N 3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-n-propan-2-ylpropanamide Chemical compound OC1=CC(CCC(=O)NC(C)C)=CC=C1N1S(=O)(=O)NC(=O)C1 MJFXNCSBCSGTCI-UHFFFAOYSA-N 0.000 claims description 3
• AJCLGITYXBNTOX-CQSZACIVSA-N 5-[2-hydroxy-4-[[(3s)-1-oxo-2,3-dihydro-2-benzazepin-3-yl]methyl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC(C[C@H]2C=CC3=CC=CC=C3C(=O)N2)=CC=C1N1CC(=O)NS1(=O)=O AJCLGITYXBNTOX-CQSZACIVSA-N 0.000 claims description 3
• YUILWSUYCPMPHG-IBGZPJMESA-N 5-[2-hydroxy-4-[[(7s)-5-oxo-6,7-dihydrobenzo[d][2]benzazepin-7-yl]methyl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC(C[C@H]2C3=CC=CC=C3C3=CC=CC=C3C(=O)N2)=CC=C1N1CC(=O)NS1(=O)=O YUILWSUYCPMPHG-IBGZPJMESA-N 0.000 claims description 3
• 239000005711 Benzoic acid Substances 0.000 claims description 3
• 230000003579 anti-obesity Effects 0.000 claims description 3
• 150000004702 methyl esters Chemical class 0.000 claims description 3
• YALYPYKJNCISOT-UHFFFAOYSA-N n-[4-(2-cyano-3-hydroxyphenoxy)butyl]-3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanamide Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCC(=O)NCCCCOC1=CC=CC(O)=C1C#N YALYPYKJNCISOT-UHFFFAOYSA-N 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• BBTVPHLHSXVLTO-KRWDZBQOSA-N tert-butyl n-[(2s)-1-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-3-phenylpropan-2-yl]carbamate Chemical compound C([C@H](NC(=O)OC(C)(C)C)CC=1C=C(O)C(N2S(NC(=O)C2)(=O)=O)=CC=1)C1=CC=CC=C1 BBTVPHLHSXVLTO-KRWDZBQOSA-N 0.000 claims description 3
• CTVKFZAEMPQAAD-QHCPKHFHSA-N (2s)-2-(benzenesulfonamido)-3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-n-(4-phenylbutyl)propanamide Chemical compound N([C@@H](CC=1C=C(C(=CC=1)N1S(NC(=O)C1)(=O)=O)O)C(=O)NCCCCC=1C=CC=CC=1)S(=O)(=O)C1=CC=CC=C1 CTVKFZAEMPQAAD-QHCPKHFHSA-N 0.000 claims description 2
• JKSQTZKTGSBKFH-SFHVURJKSA-N (2s)-2-(benzenesulfonamido)-3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-n-pentylpropanamide Chemical compound C([C@@H](C(=O)NCCCCC)NS(=O)(=O)C=1C=CC=CC=1)C(C=C1O)=CC=C1N1CC(=O)NS1(=O)=O JKSQTZKTGSBKFH-SFHVURJKSA-N 0.000 claims description 2
• BSUDYSLSZIHEET-UHFFFAOYSA-N 1-cyclohexyl-3-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]urea Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCCNC(=O)NC1CCCCC1 BSUDYSLSZIHEET-UHFFFAOYSA-N 0.000 claims description 2
• WYIRTWVMHVUSCR-UHFFFAOYSA-N 2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenoxy]acetic acid Chemical compound OC1=CC(OCC(=O)O)=CC=C1N1S(=O)(=O)NC(=O)C1 WYIRTWVMHVUSCR-UHFFFAOYSA-N 0.000 claims description 2
• QEUWRLRNIULBFS-UHFFFAOYSA-N 2-hydroxy-5-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethylsulfamoyl]benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(S(=O)(=O)NCCC=2C=C(O)C(N3S(NC(=O)C3)(=O)=O)=CC=2)=C1 QEUWRLRNIULBFS-UHFFFAOYSA-N 0.000 claims description 2
• UCMSAMKSMPNRHN-UHFFFAOYSA-N 3-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]-1,1-bis(2-methoxyethyl)urea morpholine-4-carboxylic acid Chemical compound N1(CCOCC1)C(=O)O.OC=1C=C(C=CC1N1S(NC(C1)=O)(=O)=O)CCNC(N(CCOC)CCOC)=O UCMSAMKSMPNRHN-UHFFFAOYSA-N 0.000 claims description 2
• WTSZTNRWGKZFCA-UHFFFAOYSA-N 3-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC(CCC=2C=C(O)C(N3S(NC(=O)C3)(=O)=O)=CC=2)=C1 WTSZTNRWGKZFCA-UHFFFAOYSA-N 0.000 claims description 2
• IEEQUPICLVOTGE-UHFFFAOYSA-N 3-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]benzamide 3-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]-N-methylbenzamide Chemical compound NC(=O)C1=CC=CC(CCC=2C=C(O)C(N3S(NC(=O)C3)(=O)=O)=CC=2)=C1.CNC(=O)C1=CC=CC(CCC=2C=C(O)C(N3S(NC(=O)C3)(=O)=O)=CC=2)=C1 IEEQUPICLVOTGE-UHFFFAOYSA-N 0.000 claims description 2
• KTZOIQGFYCZTNL-UHFFFAOYSA-N 3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-n-(4-phenoxybutyl)propanamide Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCC(=O)NCCCCOC1=CC=CC=C1 KTZOIQGFYCZTNL-UHFFFAOYSA-N 0.000 claims description 2
• PXZYZOCNBCFTLM-UHFFFAOYSA-N 3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-n-(5-phenylpentyl)propanamide Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCC(=O)NCCCCCC1=CC=CC=C1 PXZYZOCNBCFTLM-UHFFFAOYSA-N 0.000 claims description 2
• OGGQYJIYAXVZSA-UHFFFAOYSA-N 3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-n-[4-[2-(trifluoromethyl)phenoxy]butyl]propanamide Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCC(=O)NCCCCOC1=CC=CC=C1C(F)(F)F OGGQYJIYAXVZSA-UHFFFAOYSA-N 0.000 claims description 2
• AEYNNIYVZVOYOA-UHFFFAOYSA-N 3-[4-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethylsulfamoyl]phenyl]propanoic acid Chemical compound C1=CC(CCC(=O)O)=CC=C1S(=O)(=O)NCCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 AEYNNIYVZVOYOA-UHFFFAOYSA-N 0.000 claims description 2
• MMKKKMMLCPIUJV-UHFFFAOYSA-N 3-amino-n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]benzenesulfonamide Chemical compound NC1=CC=CC(S(=O)(=O)NCCCC=2C=C(O)C(N3S(NC(=O)C3)(=O)=O)=CC=2)=C1 MMKKKMMLCPIUJV-UHFFFAOYSA-N 0.000 claims description 2
• DVCGSNBQLWXKRC-UHFFFAOYSA-N 4-fluoro-n-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]benzamide;n-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]benzamide Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCNC(=O)C1=CC=CC=C1.C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCNC(=O)C1=CC=C(F)C=C1 DVCGSNBQLWXKRC-UHFFFAOYSA-N 0.000 claims description 2
• JKZWJFMJYJIYAB-UHFFFAOYSA-N 4-fluoro-n-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]benzenesulfonamide Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCNS(=O)(=O)C1=CC=C(F)C=C1 JKZWJFMJYJIYAB-UHFFFAOYSA-N 0.000 claims description 2
• SZAAATQVLUDOMJ-UHFFFAOYSA-N 5-(2-hydroxy-4,6-dimethylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC(C)=CC(C)=C1N1S(=O)(=O)NC(=O)C1 SZAAATQVLUDOMJ-UHFFFAOYSA-N 0.000 claims description 2
• WQHSQKTWEGOOQM-UHFFFAOYSA-N 5-(2-hydroxy-4-methylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC(C)=CC=C1N1S(=O)(=O)NC(=O)C1 WQHSQKTWEGOOQM-UHFFFAOYSA-N 0.000 claims description 2
• IDDOLRRGLNINEB-UHFFFAOYSA-N 5-(3,5-difluoro-2-hydroxy-4-methylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=C(F)C(C)=C(F)C=C1N1S(=O)(=O)NC(=O)C1 IDDOLRRGLNINEB-UHFFFAOYSA-N 0.000 claims description 2
• JFXDEXNVMSYJAN-UHFFFAOYSA-N 5-(4,5-difluoro-2-hydroxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC(F)=C(F)C=C1N1S(=O)(=O)NC(=O)C1 JFXDEXNVMSYJAN-UHFFFAOYSA-N 0.000 claims description 2
• ZULSFZYJMOBPIO-UHFFFAOYSA-N 5-(4-chloro-2-hydroxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC(Cl)=CC=C1N1S(=O)(=O)NC(=O)C1 ZULSFZYJMOBPIO-UHFFFAOYSA-N 0.000 claims description 2
• WWCVFGJUSZZUCA-UHFFFAOYSA-N 5-[2-hydroxy-4-(2-pyridin-3-ylethyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCC1=CC=CN=C1 WWCVFGJUSZZUCA-UHFFFAOYSA-N 0.000 claims description 2
• KBXWDGBWORDSIT-UHFFFAOYSA-N 5-[2-hydroxy-4-(3-hydroxyphenyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one 2-[4-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]phenyl]acetic acid Chemical compound Oc1cccc(c1)-c1ccc(N2CC(=O)NS2(=O)=O)c(O)c1.OC(=O)Cc1ccc(cc1)-c1ccc(N2CC(=O)NS2(=O)=O)c(O)c1 KBXWDGBWORDSIT-UHFFFAOYSA-N 0.000 claims description 2
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• MDMKCTUCWTWOCH-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-4-(trifluoromethoxy)benzenesulfonamide Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCCNS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 MDMKCTUCWTWOCH-UHFFFAOYSA-N 0.000 claims description 2
• KFMZUCPAQJJRMX-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-4-propan-2-ylbenzenesulfonamide Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)NCCCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 KFMZUCPAQJJRMX-UHFFFAOYSA-N 0.000 claims description 2
• JNQFZJXXUGEPJZ-UHFFFAOYSA-N n-[4-(2-hydroxyphenoxy)butyl]-3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanamide Chemical compound OC1=CC=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 JNQFZJXXUGEPJZ-UHFFFAOYSA-N 0.000 claims description 2
• KXKUMXYPNUSYJV-UHFFFAOYSA-N n-[4-(3-hydroxy-2-methoxyphenoxy)butyl]-3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanamide Chemical compound COC1=C(O)C=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 KXKUMXYPNUSYJV-UHFFFAOYSA-N 0.000 claims description 2
• UYVRHHKJWRAZDW-UHFFFAOYSA-N n-[4-(3-hydroxy-2-methylphenoxy)butyl]-3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanamide Chemical compound CC1=C(O)C=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 UYVRHHKJWRAZDW-UHFFFAOYSA-N 0.000 claims description 2
• ZRQYTWWVCOPTQZ-UHFFFAOYSA-N n-[4-(3-hydroxy-2-methylsulfinylphenoxy)butyl]-3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanamide Chemical compound CS(=O)C1=C(O)C=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 ZRQYTWWVCOPTQZ-UHFFFAOYSA-N 0.000 claims description 2
• UQBMJVFATJAOAS-UHFFFAOYSA-N n-[4-(3-hydroxy-2-methylsulfonylphenoxy)butyl]-3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanamide Chemical compound CS(=O)(=O)C1=C(O)C=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 UQBMJVFATJAOAS-UHFFFAOYSA-N 0.000 claims description 2
• FWUMNMSROBFBHO-UHFFFAOYSA-N tert-butyl 2-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]azepane-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCCC1CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 FWUMNMSROBFBHO-UHFFFAOYSA-N 0.000 claims description 2
• JXGPDPAAMYEBFR-UHFFFAOYSA-N tert-butyl 3-[[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]methyl]piperidine-1-carboxylate;5-[2-hydroxy-4-(piperidin-3-ylmethyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CC1CCCNC1.C1N(C(=O)OC(C)(C)C)CCCC1CC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 JXGPDPAAMYEBFR-UHFFFAOYSA-N 0.000 claims description 2
• YKHUFFZIITUOAK-UHFFFAOYSA-N tert-butyl n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanoylamino]carbamate Chemical compound OC1=CC(CCC(=O)NNC(=O)OC(C)(C)C)=CC=C1N1S(=O)(=O)NC(=O)C1 YKHUFFZIITUOAK-UHFFFAOYSA-N 0.000 claims description 2
• 230000004770 neurodegeneration Effects 0.000 claims 4
• 208000015181 infectious disease Diseases 0.000 claims 3
• PEKGURBKPUBLJS-UHFFFAOYSA-N 2-[4-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanoylamino]butoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 PEKGURBKPUBLJS-UHFFFAOYSA-N 0.000 claims 2
• YTWZUAQRQHUBTK-UHFFFAOYSA-N 1-(1-adamantyl)-3-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]urea Chemical compound OC1=CC(CCNC(=O)NC23CC4CC(CC(C4)C2)C3)=CC=C1N1CC(=O)NS1(=O)=O YTWZUAQRQHUBTK-UHFFFAOYSA-N 0.000 claims 1
• JYGTUJRISQMVML-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]urea Chemical compound OC1=CC(CCNC(=O)NCCO)=CC=C1N1S(=O)(=O)NC(=O)C1 JYGTUJRISQMVML-UHFFFAOYSA-N 0.000 claims 1
• YYDJBNIEUFUSII-UHFFFAOYSA-N 1-(benzenesulfonyl)-1-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]urea Chemical compound C=1C=CC=CC=1S(=O)(=O)N(C(=O)N)CCC(C=C1O)=CC=C1N1CC(=O)NS1(=O)=O YYDJBNIEUFUSII-UHFFFAOYSA-N 0.000 claims 1
• HZVMRNXUXYSWEH-UHFFFAOYSA-N 1-[(2,4-dimethoxyphenyl)methyl]-3-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]urea Chemical compound COC1=CC(OC)=CC=C1CNC(=O)NCCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 HZVMRNXUXYSWEH-UHFFFAOYSA-N 0.000 claims 1
• FWJORRKUHKTJJT-UHFFFAOYSA-N 2,2-diphenylethanesulfonic acid;n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-2,5-bis(2,2,2-trifluoroethoxy)benzenesulfonamide Chemical compound C=1C=CC=CC=1C(CS(=O)(=O)O)C1=CC=CC=C1.C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCCNS(=O)(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F FWJORRKUHKTJJT-UHFFFAOYSA-N 0.000 claims 1
• GYHOBVJJPIJJSH-UHFFFAOYSA-N 2-[4-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanoylamino]butoxy]-N,N,6-trimethylbenzamide Chemical compound OC=1C=C(C=CC=1N1S(NC(C1)=O)(=O)=O)CCC(=O)NCCCCOC1=C(C(=O)N(C)C)C(=CC=C1)C GYHOBVJJPIJJSH-UHFFFAOYSA-N 0.000 claims 1
• KDRBAKYYQGGSHO-UHFFFAOYSA-N 2-fluoro-6-[4-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanoylamino]butoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=C(F)C=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 KDRBAKYYQGGSHO-UHFFFAOYSA-N 0.000 claims 1
• MPUSDZLIFSAKPE-UHFFFAOYSA-N 3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-n-[4-(2-methylsulfonylphenoxy)butyl]propanamide Chemical compound CS(=O)(=O)C1=CC=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 MPUSDZLIFSAKPE-UHFFFAOYSA-N 0.000 claims 1
• VHMJYOPAGKKCFK-UHFFFAOYSA-N 3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-n-[4-(3-methoxyphenoxy)butyl]propanamide Chemical compound COC1=CC=CC(OCCCCNC(=O)CCC=2C=C(O)C(N3S(NC(=O)C3)(=O)=O)=CC=2)=C1 VHMJYOPAGKKCFK-UHFFFAOYSA-N 0.000 claims 1
• RCPXLUBHMWZQDD-UHFFFAOYSA-N 4-fluoro-n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]benzamide;n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]acetamide Chemical compound OC1=CC(CCCNC(=O)C)=CC=C1N1S(=O)(=O)NC(=O)C1.C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCCNC(=O)C1=CC=C(F)C=C1 RCPXLUBHMWZQDD-UHFFFAOYSA-N 0.000 claims 1
• RPEKVCBNWQFLOY-UHFFFAOYSA-N 5-[2-hydroxy-4-(2-quinolin-3-ylethyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC(CCC=2C=C3C=CC=CC3=NC=2)=CC=C1N1CC(=O)NS1(=O)=O RPEKVCBNWQFLOY-UHFFFAOYSA-N 0.000 claims 1
• NGCNOJYCXLKVBL-UHFFFAOYSA-N 5-[2-hydroxy-4-(methylsulfanylmethyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one;5-[2-hydroxy-4-(propan-2-ylsulfinylmethyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC(CSC)=CC=C1N1S(=O)(=O)NC(=O)C1.OC1=CC(CS(=O)C(C)C)=CC=C1N1S(=O)(=O)NC(=O)C1 NGCNOJYCXLKVBL-UHFFFAOYSA-N 0.000 claims 1
• YVNXDBHMMYJDPJ-UHFFFAOYSA-N 5-[2-hydroxy-4-(pyrazol-1-ylmethyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one 5-[2-hydroxy-4-[[3-(trifluoromethyl)pyrazol-1-yl]methyl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=C(C=CC(=C1)CN1N=C(C=C1)C(F)(F)F)N1CC(NS1(=O)=O)=O.OC1=C(C=CC(=C1)CN1N=CC=C1)N1CC(NS1(=O)=O)=O YVNXDBHMMYJDPJ-UHFFFAOYSA-N 0.000 claims 1
• ORANRQRCXDWOKA-UHFFFAOYSA-N 5-[2-hydroxy-4-[(1-hydroxy-2,3-dihydro-1H-inden-2-yl)methyl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one 5-[2-hydroxy-4-(3-hydroxy-2-methoxy-3-phenylpropyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=C(C=CC(=C1)CC(C(C1=CC=CC=C1)O)OC)N1CC(NS1(=O)=O)=O.OC1=C(C=CC(=C1)CC1C(C2=CC=CC=C2C1)O)N1CC(NS1(=O)=O)=O ORANRQRCXDWOKA-UHFFFAOYSA-N 0.000 claims 1
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• FHWJMLYOMAXLMD-UHFFFAOYSA-N 5-[2-hydroxy-4-[2-(2-propyl-1,3-thiazol-5-yl)ethyl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound S1C(CCC)=NC=C1CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 FHWJMLYOMAXLMD-UHFFFAOYSA-N 0.000 claims 1
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• VWGUKYVRFRKFMB-UHFFFAOYSA-N 5-[2-hydroxy-4-[2-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethyl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CCC(C=C1O)=CC=C1N1CC(=O)NS1(=O)=O VWGUKYVRFRKFMB-UHFFFAOYSA-N 0.000 claims 1
• DBFMVOCOAOYXMW-UHFFFAOYSA-N 5-[4-(2-benzoylbutyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one;5-[4-(2-benzoylpentyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C=1C=CC=CC=1C(=O)C(CC)CC(C=C1O)=CC=C1N1CC(=O)NS1(=O)=O.C=1C=CC=CC=1C(=O)C(CCC)CC(C=C1O)=CC=C1N1CC(=O)NS1(=O)=O DBFMVOCOAOYXMW-UHFFFAOYSA-N 0.000 claims 1
• KSNZGEGCMAKLPI-UHFFFAOYSA-N 5-[4-(2-benzyl-3-oxo-3-phenylpropyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one 5-[2-hydroxy-4-(3-oxo-2,3-diphenylpropyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C(C1=CC=CC=C1)C(CC1=CC(=C(C=C1)N1CC(NS1(=O)=O)=O)O)C(C1=CC=CC=C1)=O.OC1=C(C=CC(=C1)CC(C(C1=CC=CC=C1)=O)C1=CC=CC=C1)N1CC(NS1(=O)=O)=O KSNZGEGCMAKLPI-UHFFFAOYSA-N 0.000 claims 1
• ILCZSPUCQCNJML-UHFFFAOYSA-N 5-[4-(3,3-dimethylbutyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one 5-[2-hydroxy-4-(3,3,3-trifluoropropyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=C(C=CC(=C1)CCC(F)(F)F)N1CC(NS1(=O)=O)=O.CC(CCC1=CC(=C(C=C1)N1CC(NS1(=O)=O)=O)O)(C)C ILCZSPUCQCNJML-UHFFFAOYSA-N 0.000 claims 1
• HOKUGSQIFGMEIH-UHFFFAOYSA-N 5-[4-(benzenesulfonyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one 5-[2-hydroxy-4-(trifluoromethyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=C(C=CC(=C1)C(F)(F)F)N1CC(NS1(=O)=O)=O.C1(=CC=CC=C1)S(=O)(=O)C1=CC(=C(C=C1)N1CC(NS1(=O)=O)=O)O HOKUGSQIFGMEIH-UHFFFAOYSA-N 0.000 claims 1
• IBRNBDRULCBMAW-UHFFFAOYSA-N 5-[4-(cyclohexylmethyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one 5-[4-(cyclopentylmethyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1(CCCCC1)CC1=CC(=C(C=C1)N1CC(NS1(=O)=O)=O)O.C1(CCCC1)CC1=CC(=C(C=C1)N1CC(NS1(=O)=O)=O)O IBRNBDRULCBMAW-UHFFFAOYSA-N 0.000 claims 1
• QSROXJRAVVBHIZ-UHFFFAOYSA-N 5-[4-[2-(1,1-dioxothiazinan-3-yl)ethyl]-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCC1CCCS(=O)(=O)N1 QSROXJRAVVBHIZ-UHFFFAOYSA-N 0.000 claims 1
• BZZTWYTWBZWYHO-UHFFFAOYSA-N 5-[4-[2-(2-aminophenyl)propyl]-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one;ethyl 3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-2-phenylpropanoate Chemical compound C=1C=CC=C(N)C=1C(C)CC(C=C1O)=CC=C1N1CC(=O)NS1(=O)=O.C=1C=CC=CC=1C(C(=O)OCC)CC(C=C1O)=CC=C1N1CC(=O)NS1(=O)=O BZZTWYTWBZWYHO-UHFFFAOYSA-N 0.000 claims 1
• VXZAJZVAOBRCHW-UHFFFAOYSA-N 5-[4-[2-(2-benzylsulfonyl-3,4-dihydro-1h-isoquinolin-3-yl)ethyl]-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCC1CC2=CC=CC=C2CN1S(=O)(=O)CC1=CC=CC=C1 VXZAJZVAOBRCHW-UHFFFAOYSA-N 0.000 claims 1
• QWAVTSRKYXUPFQ-UHFFFAOYSA-N 5-[4-[[2-(aminomethyl)phenyl]methyl]-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one;5-[2-hydroxy-4-[[2-(methoxymethyl)phenyl]methyl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound NCC1=CC=CC=C1CC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1.COCC1=CC=CC=C1CC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 QWAVTSRKYXUPFQ-UHFFFAOYSA-N 0.000 claims 1
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