BRPI0619547A2 - 1,1,3-trioxo-1,2,5-tiadiazolidinas, composição farmacêutica e uso das mesmas - Google Patents

Info

Publication number

BRPI0619547A2

BRPI0619547A2 BRPI0619547-4A BRPI0619547A BRPI0619547A2 BR PI0619547 A2 BRPI0619547 A2 BR PI0619547A2 BR PI0619547 A BRPI0619547 A BR PI0619547A BR PI0619547 A2 BRPI0619547 A2 BR PI0619547A2

Authority

BR

Brazil

Prior art keywords

thiadiazolidin

hydroxy

dioxo

phenyl

trioxo

Prior art date

2005-12-08

Links

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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 28
• JSZAZZQHDRHICK-UHFFFAOYSA-N 1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical class O=C1CNS(=O)(=O)N1 JSZAZZQHDRHICK-UHFFFAOYSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 215
• 230000000694 effects Effects 0.000 claims abstract description 30
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 29
• 102000002727 Protein Tyrosine Phosphatase Human genes 0.000 claims abstract description 22
• 108020000494 protein-tyrosine phosphatase Proteins 0.000 claims abstract description 22
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
• 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 18
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 18
• 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 17
• 208000017170 Lipid metabolism disease Diseases 0.000 claims abstract description 17
• 230000001404 mediated effect Effects 0.000 claims abstract description 15
• 206010020772 Hypertension Diseases 0.000 claims abstract description 12
• 201000010099 disease Diseases 0.000 claims abstract description 12
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 11
• 208000035473 Communicable disease Diseases 0.000 claims abstract description 11
• 208000002705 Glucose Intolerance Diseases 0.000 claims abstract description 11
• 206010018429 Glucose tolerance impaired 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
• 210000004204 blood vessel Anatomy 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
• 208000002551 irritable bowel syndrome 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
• 208000023589 ischemic disease Diseases 0.000 claims abstract description 10
• 230000002792 vascular Effects 0.000 claims abstract description 10
• -1 amino, carbamoyl Chemical group 0.000 claims description 171
• 150000003839 salts Chemical class 0.000 claims description 78
• 125000000623 heterocyclic group Chemical group 0.000 claims description 72
• 239000001257 hydrogen Substances 0.000 claims description 72
• 229910052739 hydrogen Inorganic materials 0.000 claims description 72
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• 125000003118 aryl group Chemical group 0.000 claims description 60
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 58
• 238000000034 method Methods 0.000 claims description 51
• 125000003545 alkoxy group Chemical group 0.000 claims description 44
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
• 150000002367 halogens Chemical group 0.000 claims description 35
• 229910052736 halogen Inorganic materials 0.000 claims description 34
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
• 125000004414 alkyl thio group Chemical group 0.000 claims description 33
• 125000001424 substituent group Chemical group 0.000 claims description 32
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
• 125000003282 alkyl amino group Chemical group 0.000 claims description 28
• 125000004104 aryloxy group Chemical group 0.000 claims description 28
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 28
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 23
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 23
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
• 125000002252 acyl group Chemical group 0.000 claims description 19
• 150000002431 hydrogen Chemical group 0.000 claims description 19
• 125000004423 acyloxy group Chemical group 0.000 claims description 18
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 17
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 16
• 125000003342 alkenyl group Chemical group 0.000 claims description 15
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 14
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
• 125000005110 aryl thio group Chemical group 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• 229940098779 methanesulfonic acid Drugs 0.000 claims description 12
• 241000124008 Mammalia Species 0.000 claims description 11
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 239000003472 antidiabetic agent Substances 0.000 claims description 10
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
• 239000000883 anti-obesity agent Substances 0.000 claims description 9
• 229940125710 antiobesity agent Drugs 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 238000002360 preparation method Methods 0.000 claims description 8
• 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 7
• 125000002947 alkylene group Chemical group 0.000 claims description 7
• 229940125708 antidiabetic agent Drugs 0.000 claims description 7
• 229940030600 antihypertensive agent Drugs 0.000 claims description 7
• 239000002220 antihypertensive agent Substances 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
• 239000003524 antilipemic agent Substances 0.000 claims description 6
• 150000001721 carbon Chemical group 0.000 claims description 6
• 239000008103 glucose Substances 0.000 claims description 6
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 150000003573 thiols Chemical class 0.000 claims description 6
• NUUGJBWUSWUPSK-UHFFFAOYSA-N 5-(5-benzyl-2-hydroxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=C1CC1=CC=CC=C1 NUUGJBWUSWUPSK-UHFFFAOYSA-N 0.000 claims description 5
• BRBWNUSCQLSUKY-UHFFFAOYSA-N 5-[2-hydroxy-5-(5-methylhexyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC(C)CCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 BRBWNUSCQLSUKY-UHFFFAOYSA-N 0.000 claims description 5
• 239000005711 Benzoic acid Substances 0.000 claims description 5
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
• 235000010233 benzoic acid Nutrition 0.000 claims description 5
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
• VSIYWWQPRQBIAN-UHFFFAOYSA-N 5-(2-hydroxy-5-methylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 VSIYWWQPRQBIAN-UHFFFAOYSA-N 0.000 claims description 4
• FKUDRPZPTZZZRO-UHFFFAOYSA-N 5-(2-hydroxy-5-phenoxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=C1OC1=CC=CC=C1 FKUDRPZPTZZZRO-UHFFFAOYSA-N 0.000 claims description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
• 239000004202 carbamide Substances 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 229910052702 rhenium Inorganic materials 0.000 claims description 4
• SJASLNFSSMKCIZ-UHFFFAOYSA-N 5-(2-hydroxy-5-methoxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound COC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 SJASLNFSSMKCIZ-UHFFFAOYSA-N 0.000 claims description 3
• VYWYAKUXRWUPRZ-UHFFFAOYSA-N 5-(5-butyl-2-hydroxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 VYWYAKUXRWUPRZ-UHFFFAOYSA-N 0.000 claims description 3
• FERPKFJGOABLOY-UHFFFAOYSA-N 5-(5-hexyl-2-hydroxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CCCCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 FERPKFJGOABLOY-UHFFFAOYSA-N 0.000 claims description 3
• IJQLYBWGZSEZFQ-UHFFFAOYSA-N 5-[2-hydroxy-5-(oxolan-3-yl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C2COCC2)C=C1N1CC(=O)NS1(=O)=O IJQLYBWGZSEZFQ-UHFFFAOYSA-N 0.000 claims description 3
• BCCUWNVAKXXYAV-UHFFFAOYSA-N 5-[4-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]pyrazol-1-yl]pentanoic acid Chemical compound C1=NN(CCCCC(=O)O)C=C1C1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 BCCUWNVAKXXYAV-UHFFFAOYSA-N 0.000 claims description 3
• KFVZNMFATSFUIA-UHFFFAOYSA-N 5-[5-[(benzylamino)methyl]-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=C1CNCC1=CC=CC=C1 KFVZNMFATSFUIA-UHFFFAOYSA-N 0.000 claims description 3
• GRWJKKRWMZCFAG-UHFFFAOYSA-N 5-[5-[2-(4-fluorophenyl)ethynyl]-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C#CC=2C=CC(F)=CC=2)C=C1N1CC(=O)NS1(=O)=O GRWJKKRWMZCFAG-UHFFFAOYSA-N 0.000 claims description 3
• TZTOTGASJUSLPV-UHFFFAOYSA-N 6-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]hexanoic acid Chemical compound OC(=O)CCCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 TZTOTGASJUSLPV-UHFFFAOYSA-N 0.000 claims description 3
• 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 3
• 230000002401 inhibitory effect Effects 0.000 claims description 3
• WWINNRASOUAADD-UHFFFAOYSA-N methyl 3-[3-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]phenyl]propanoate Chemical compound COC(=O)CCC1=CC=CC(C=2C=C(C(O)=CC=2)N2S(NC(=O)C2)(=O)=O)=C1 WWINNRASOUAADD-UHFFFAOYSA-N 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 2
• SDYONCWKEINECK-UHFFFAOYSA-N 2-[3-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]phenyl]acetonitrile Chemical compound OC1=CC=C(C=2C=C(CC#N)C=CC=2)C=C1N1CC(=O)NS1(=O)=O SDYONCWKEINECK-UHFFFAOYSA-N 0.000 claims description 2
• QVZDAUYSRZFWKD-UHFFFAOYSA-N 2-[4-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 QVZDAUYSRZFWKD-UHFFFAOYSA-N 0.000 claims description 2
• XUVOULBEMLKKLS-UHFFFAOYSA-N 2-[5-(4-fluorophenyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C=2C=CC(F)=CC=2)C=C1N1C(=O)CNS1(=O)=O XUVOULBEMLKKLS-UHFFFAOYSA-N 0.000 claims description 2
• VXGWQGJMGATGNU-UHFFFAOYSA-N 3-[3-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]phenyl]propanoic acid Chemical compound OC(=O)CCC1=CC=CC(C=2C=C(C(O)=CC=2)N2S(NC(=O)C2)(=O)=O)=C1 VXGWQGJMGATGNU-UHFFFAOYSA-N 0.000 claims description 2
• UVSFCDQPTVMDRL-UHFFFAOYSA-N 5-[2-hydroxy-5-[1-(3-methylbutyl)pyrazol-4-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=NN(CCC(C)C)C=C1C1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 UVSFCDQPTVMDRL-UHFFFAOYSA-N 0.000 claims description 2
• WUJLLDAJOIZQHU-UHFFFAOYSA-N 5-[2-hydroxy-5-[1-(4,4,4-trifluorobutyl)pyrazol-4-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C2=CN(CCCC(F)(F)F)N=C2)C=C1N1CC(=O)NS1(=O)=O WUJLLDAJOIZQHU-UHFFFAOYSA-N 0.000 claims description 2
• ACHPHGFXNHGXCP-UHFFFAOYSA-N 5-[4-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]pyrazol-1-yl]pentanenitrile Chemical compound OC1=CC=C(C2=CN(CCCCC#N)N=C2)C=C1N1CC(=O)NS1(=O)=O ACHPHGFXNHGXCP-UHFFFAOYSA-N 0.000 claims description 2
• HQSPFMHPCAHPRX-UHFFFAOYSA-N 5-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-2,2-dimethylpentanoic acid Chemical compound OC(=O)C(C)(C)CCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 HQSPFMHPCAHPRX-UHFFFAOYSA-N 0.000 claims description 2
• LNGWSPCBDDIQCH-UHFFFAOYSA-N 5-[5-(3,3-dimethylbut-1-ynyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC(C)(C)C#CC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 LNGWSPCBDDIQCH-UHFFFAOYSA-N 0.000 claims description 2
• XJEQFAYMKGZHHE-UHFFFAOYSA-N 6-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-2,2-dimethylhexanoic acid Chemical compound OC(=O)C(C)(C)CCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 XJEQFAYMKGZHHE-UHFFFAOYSA-N 0.000 claims description 2
• QZFXPVZMHTUOHA-UHFFFAOYSA-N 6-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]hex-5-ynoic acid Chemical compound OC(=O)CCCC#CC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 QZFXPVZMHTUOHA-UHFFFAOYSA-N 0.000 claims description 2
• UGDTZJVSFIMFFE-UHFFFAOYSA-N 7-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-2,2-dimethylheptanoic acid Chemical compound OC(=O)C(C)(C)CCCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 UGDTZJVSFIMFFE-UHFFFAOYSA-N 0.000 claims description 2
• YQIVMNCHDVGODK-UHFFFAOYSA-N 8-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-2,2-dimethyloctanoic acid Chemical compound OC(=O)C(C)(C)CCCCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 YQIVMNCHDVGODK-UHFFFAOYSA-N 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• VGTQEJGDMYPUFH-UHFFFAOYSA-N benzyl n-[[3-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]phenyl]methyl]carbamate Chemical compound OC1=CC=C(C=2C=C(CNC(=O)OCC=3C=CC=CC=3)C=CC=2)C=C1N1CC(=O)NS1(=O)=O VGTQEJGDMYPUFH-UHFFFAOYSA-N 0.000 claims description 2
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• YVEBUOQGWIOXIQ-UHFFFAOYSA-N ethyl 3-[3-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]phenyl]propanoate Chemical compound CCOC(=O)CCC1=CC=CC(C=2C=C(C(O)=CC=2)N2S(NC(=O)C2)(=O)=O)=C1 YVEBUOQGWIOXIQ-UHFFFAOYSA-N 0.000 claims description 2
• QJXIYZCWOSBYFC-UHFFFAOYSA-N ethyl 7-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-2,2-dimethylheptanoate Chemical compound CCOC(=O)C(C)(C)CCCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 QJXIYZCWOSBYFC-UHFFFAOYSA-N 0.000 claims description 2
• JEZFRVZFQQOFSI-UHFFFAOYSA-N ethyl 8-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-2,2-dimethyloctanoate Chemical compound CCOC(=O)C(C)(C)CCCCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 JEZFRVZFQQOFSI-UHFFFAOYSA-N 0.000 claims description 2
• 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims description 2
• XDHLXWMRMKISCM-UHFFFAOYSA-N methyl n-[[3-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]phenyl]methyl]carbamate Chemical compound COC(=O)NCC1=CC=CC(C=2C=C(C(O)=CC=2)N2S(NC(=O)C2)(=O)=O)=C1 XDHLXWMRMKISCM-UHFFFAOYSA-N 0.000 claims description 2
• XXMOBFZXWLDPED-UHFFFAOYSA-N n-(2-cyanoethyl)-3-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]benzamide Chemical compound OC1=CC=C(C=2C=C(C=CC=2)C(=O)NCCC#N)C=C1N1CC(=O)NS1(=O)=O XXMOBFZXWLDPED-UHFFFAOYSA-N 0.000 claims description 2
• HBAYYSDYCMFNKK-UHFFFAOYSA-N n-[[3-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]phenyl]methyl]acetamide Chemical compound CC(=O)NCC1=CC=CC(C=2C=C(C(O)=CC=2)N2S(NC(=O)C2)(=O)=O)=C1 HBAYYSDYCMFNKK-UHFFFAOYSA-N 0.000 claims description 2
• 230000004770 neurodegeneration Effects 0.000 claims 4
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• IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 claims 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• IZMXHZGMYGCQOW-UHFFFAOYSA-N 4-[4-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]pyrazol-1-yl]butanenitrile Chemical compound OC1=CC=C(C2=CN(CCCC#N)N=C2)C=C1N1CC(=O)NS1(=O)=O IZMXHZGMYGCQOW-UHFFFAOYSA-N 0.000 claims 1
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• 101710128896 Tyrosine-protein phosphatase non-receptor type 1 Proteins 0.000 claims 1
• 239000003963 antioxidant agent Substances 0.000 claims 1
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
• 208000031225 myocardial ischemia Diseases 0.000 claims 1
• BPYZTPAVGRGAEL-UHFFFAOYSA-N n-(3-amino-3-oxopropyl)-3-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]benzamide Chemical compound NC(=O)CCNC(=O)C1=CC=CC(C=2C=C(C(O)=CC=2)N2S(NC(=O)C2)(=O)=O)=C1 BPYZTPAVGRGAEL-UHFFFAOYSA-N 0.000 claims 1
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 1
• 239000003112 inhibitor Substances 0.000 abstract description 17
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• DCWXELXMIBXGTH-UHFFFAOYSA-N phosphotyrosine Chemical compound OC(=O)C(N)CC1=CC=C(OP(O)(O)=O)C=C1 DCWXELXMIBXGTH-UHFFFAOYSA-N 0.000 abstract 1
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