RU2008143053A - Тиадиазолидиноновые ингибиторы птфазы - Google Patents
Тиадиазолидиноновые ингибиторы птфазы Download PDFInfo
- Publication number
- RU2008143053A RU2008143053A RU2008143053/04A RU2008143053A RU2008143053A RU 2008143053 A RU2008143053 A RU 2008143053A RU 2008143053/04 A RU2008143053/04 A RU 2008143053/04A RU 2008143053 A RU2008143053 A RU 2008143053A RU 2008143053 A RU2008143053 A RU 2008143053A
- Authority
- RU
- Russia
- Prior art keywords
- thiadiazolidin
- hydroxy
- phenyl
- trioxo
- dioxo
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 31
- 125000003118 aryl group Chemical group 0.000 claims abstract 19
- 150000001875 compounds Chemical class 0.000 claims abstract 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 18
- 239000001257 hydrogen Substances 0.000 claims abstract 18
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 14
- 150000002431 hydrogen Chemical class 0.000 claims abstract 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 12
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 9
- 125000002947 alkylene group Chemical group 0.000 claims abstract 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000001589 carboacyl group Chemical group 0.000 claims abstract 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 6
- 239000001301 oxygen Substances 0.000 claims abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000005236 alkanoylamino group Chemical group 0.000 claims abstract 4
- -1 aralkoxy Chemical group 0.000 claims 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 19
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000004104 aryloxy group Chemical group 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 6
- 150000001721 carbon Chemical group 0.000 claims 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims 3
- 125000005110 aryl thio group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 125000004470 heterocyclooxy group Chemical group 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 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 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 208000002705 Glucose Intolerance Diseases 0.000 claims 2
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 206010033645 Pancreatitis Diseases 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 210000004204 blood vessel Anatomy 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 210000000987 immune system Anatomy 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 208000023589 ischemic disease Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- XSAXZNVHWVQTLU-UHFFFAOYSA-N 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=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCCNS(=O)(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F XSAXZNVHWVQTLU-UHFFFAOYSA-N 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 208000037803 restenosis Diseases 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 230000002792 vascular Effects 0.000 claims 2
- 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 1
- 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 1
- 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
- NEMVVKYGPYPVCL-UHFFFAOYSA-N 1-(1-adamantyl)-3-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]urea Chemical compound OC1=CC(CCCNC(=O)NC23CC4CC(CC(C4)C2)C3)=CC=C1N1CC(=O)NS1(=O)=O NEMVVKYGPYPVCL-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
- HFNMPRNRJKLMAS-UHFFFAOYSA-N 1-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]-3-phenylurea Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCNC(=O)NC1=CC=CC=C1 HFNMPRNRJKLMAS-UHFFFAOYSA-N 0.000 claims 1
- UEGONJOSVATMIS-UHFFFAOYSA-N 1-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]-3-piperidin-4-ylurea Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCNC(=O)NC1CCNCC1 UEGONJOSVATMIS-UHFFFAOYSA-N 0.000 claims 1
- XKLXQNFDJNYSEM-UHFFFAOYSA-N 1-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-3-phenylurea Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCCNC(=O)NC1=CC=CC=C1 XKLXQNFDJNYSEM-UHFFFAOYSA-N 0.000 claims 1
- XPULGFXFKDNDEB-UHFFFAOYSA-N 1-cyclohexyl-3-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]urea Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCNC(=O)NC1CCCCC1 XPULGFXFKDNDEB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- UBEDNMAXVLZVRU-UHFFFAOYSA-N 1-ethyl-3-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]urea Chemical compound OC1=CC(CCNC(=O)NCC)=CC=C1N1S(=O)(=O)NC(=O)C1 UBEDNMAXVLZVRU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims 1
- AGLICVGMPSHEQR-UHFFFAOYSA-N 2-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]benzonitrile Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCC1=CC=CC=C1C#N AGLICVGMPSHEQR-UHFFFAOYSA-N 0.000 claims 1
- QCVDVXGWIBTTLM-UHFFFAOYSA-N 2-[2-[[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]methyl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 QCVDVXGWIBTTLM-UHFFFAOYSA-N 0.000 claims 1
- WVXIBJQHUZZTCP-UHFFFAOYSA-N 2-[2-[[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]methyl]phenyl]acetonitrile Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CC1=CC=CC=C1CC#N WVXIBJQHUZZTCP-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- 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 1
- ZUKPPOCXBNYXOM-UHFFFAOYSA-N 2-[4-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]butyl]isoindole-1,3-dione Chemical compound OC1=CC(CCCCN2C(C3=CC=CC=C3C2=O)=O)=CC=C1N1CC(=O)NS1(=O)=O ZUKPPOCXBNYXOM-UHFFFAOYSA-N 0.000 claims 1
- VDVNVRCTKMVUSF-UHFFFAOYSA-N 2-[4-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]butylcarbamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)NCCCCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 VDVNVRCTKMVUSF-UHFFFAOYSA-N 0.000 claims 1
- PHFFSWGADPNULH-UHFFFAOYSA-N 2-[4-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 PHFFSWGADPNULH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- OTYMMOSMYKDSCP-UHFFFAOYSA-N 2-hydroxy-5-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propylsulfamoyl]benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(S(=O)(=O)NCCCC=2C=C(O)C(N3S(NC(=O)C3)(=O)=O)=CC=2)=C1 OTYMMOSMYKDSCP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- DDKNICGGRRYCEH-UHFFFAOYSA-N 3,4-dichloro-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(Cl)C(Cl)=C1 DDKNICGGRRYCEH-UHFFFAOYSA-N 0.000 claims 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
- PXYPUYOBRPFFQA-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 Chemical compound OC1=CC(CCNC(=O)N(CCOC)CCOC)=CC=C1N1S(=O)(=O)NC(=O)C1 PXYPUYOBRPFFQA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GAAILBVEADHLOO-UHFFFAOYSA-N 3-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(CCC=2C=C(O)C(N3S(NC(=O)C3)(=O)=O)=CC=2)=C1 GAAILBVEADHLOO-UHFFFAOYSA-N 0.000 claims 1
- SCSBLKIMGCTRCJ-UHFFFAOYSA-N 3-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]benzamide Chemical compound NC(=O)C1=CC=CC(CCC=2C=C(O)C(N3S(NC(=O)C3)(=O)=O)=CC=2)=C1 SCSBLKIMGCTRCJ-UHFFFAOYSA-N 0.000 claims 1
- OMZKHAKHSHGYAF-UHFFFAOYSA-N 3-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(CCC=2C=C(O)C(N3S(NC(=O)C3)(=O)=O)=CC=2)=C1 OMZKHAKHSHGYAF-UHFFFAOYSA-N 0.000 claims 1
- JVULZZFTKHBEFR-UHFFFAOYSA-N 3-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-1h-quinazoline-2,4-dione Chemical compound OC1=CC(CCCN2C(C3=CC=CC=C3NC2=O)=O)=CC=C1N1CC(=O)NS1(=O)=O JVULZZFTKHBEFR-UHFFFAOYSA-N 0.000 claims 1
- CJBRYPMTEKNUEU-UHFFFAOYSA-N 3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-n-(2-methylphenyl)propanamide Chemical compound CC1=CC=CC=C1NC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 CJBRYPMTEKNUEU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- FSFOUEIWXRZZJA-UHFFFAOYSA-N 3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-n-pentylpropanamide Chemical compound OC1=CC(CCC(=O)NCCCCC)=CC=C1N1S(=O)(=O)NC(=O)C1 FSFOUEIWXRZZJA-UHFFFAOYSA-N 0.000 claims 1
- UJPMCPPGQMSKSF-UHFFFAOYSA-N 3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-n-phenylpropanamide Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCC(=O)NC1=CC=CC=C1 UJPMCPPGQMSKSF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
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- ATIAAWCBBJYNNF-UHFFFAOYSA-N methyl 2-[2-[[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]methyl]phenyl]acetate Chemical compound COC(=O)CC1=CC=CC=C1CC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 ATIAAWCBBJYNNF-UHFFFAOYSA-N 0.000 claims 1
- RWBADMLBNJAWLT-UHFFFAOYSA-N methyl 2-[4-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanoylamino]butoxy]benzoate Chemical compound COC(=O)C1=CC=CC=C1OCCCCNC(=O)CCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 RWBADMLBNJAWLT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
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- RGELSFZKEKBVHH-UHFFFAOYSA-N methyl 3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propanoate Chemical compound OC1=CC(CCC(=O)OC)=CC=C1N1S(=O)(=O)NC(=O)C1 RGELSFZKEKBVHH-UHFFFAOYSA-N 0.000 claims 1
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- BRMGTUAFMILQLR-QWHCGFSZSA-N n-[(1r,2s)-2-[[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]methyl]cyclohexyl]methanesulfonamide Chemical compound CS(=O)(=O)N[C@@H]1CCCC[C@H]1CC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 BRMGTUAFMILQLR-QWHCGFSZSA-N 0.000 claims 1
- CIMAXEFXYONGSX-IBGZPJMESA-N n-[(1s)-1-(1h-benzimidazol-2-yl)-2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]benzenesulfonamide Chemical compound N([C@@H](CC=1C=C(C(=CC=1)N1S(NC(=O)C1)(=O)=O)O)C=1NC2=CC=CC=C2N=1)S(=O)(=O)C1=CC=CC=C1 CIMAXEFXYONGSX-IBGZPJMESA-N 0.000 claims 1
- BRMGTUAFMILQLR-OLZOCXBDSA-N n-[(1s,2r)-2-[[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]methyl]cyclohexyl]methanesulfonamide Chemical compound CS(=O)(=O)N[C@H]1CCCC[C@@H]1CC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 BRMGTUAFMILQLR-OLZOCXBDSA-N 0.000 claims 1
- VOIQBUYUASKUPI-OAQYLSRUSA-N n-[(2r)-1-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-3-phenylpropan-2-yl]-1-phenylmethanesulfonamide Chemical compound C([C@H](CC=1C=C(C(=CC=1)N1S(NC(=O)C1)(=O)=O)O)NS(=O)(=O)CC=1C=CC=CC=1)C1=CC=CC=C1 VOIQBUYUASKUPI-OAQYLSRUSA-N 0.000 claims 1
- VOIQBUYUASKUPI-NRFANRHFSA-N n-[(2s)-1-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-3-phenylpropan-2-yl]-1-phenylmethanesulfonamide Chemical compound C([C@@H](CC=1C=C(C(=CC=1)N1S(NC(=O)C1)(=O)=O)O)NS(=O)(=O)CC=1C=CC=CC=1)C1=CC=CC=C1 VOIQBUYUASKUPI-NRFANRHFSA-N 0.000 claims 1
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- VYLILWDLSZJZJM-UHFFFAOYSA-N n-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]-2,2-dimethylpropanamide Chemical compound OC1=CC(CCNC(=O)C(C)(C)C)=CC=C1N1S(=O)(=O)NC(=O)C1 VYLILWDLSZJZJM-UHFFFAOYSA-N 0.000 claims 1
- UFSMZKBIHYZXTA-UHFFFAOYSA-N n-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]-2-methylpropanamide Chemical compound OC1=CC(CCNC(=O)C(C)C)=CC=C1N1S(=O)(=O)NC(=O)C1 UFSMZKBIHYZXTA-UHFFFAOYSA-N 0.000 claims 1
- ROQSIUOYTYSJMF-UHFFFAOYSA-N n-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]acetamide Chemical compound OC1=CC(CCNC(=O)C)=CC=C1N1S(=O)(=O)NC(=O)C1 ROQSIUOYTYSJMF-UHFFFAOYSA-N 0.000 claims 1
- AXIXQUWOFXXGSL-UHFFFAOYSA-N n-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]adamantane-1-carboxamide Chemical compound OC1=CC(CCNC(=O)C23CC4CC(CC(C4)C2)C3)=CC=C1N1CC(=O)NS1(=O)=O AXIXQUWOFXXGSL-UHFFFAOYSA-N 0.000 claims 1
- DJJIINXCPZSKRJ-UHFFFAOYSA-N 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 DJJIINXCPZSKRJ-UHFFFAOYSA-N 0.000 claims 1
- JERNCWVDXCVZEU-UHFFFAOYSA-N 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=CC=C1 JERNCWVDXCVZEU-UHFFFAOYSA-N 0.000 claims 1
- YCSBCCARSNJISH-UHFFFAOYSA-N n-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]methanesulfonamide Chemical compound OC1=CC(CCNS(=O)(=O)C)=CC=C1N1S(=O)(=O)NC(=O)C1 YCSBCCARSNJISH-UHFFFAOYSA-N 0.000 claims 1
- LCULXPJDAPOLLX-UHFFFAOYSA-N n-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]propanamide Chemical compound OC1=CC(CCNC(=O)CC)=CC=C1N1S(=O)(=O)NC(=O)C1 LCULXPJDAPOLLX-UHFFFAOYSA-N 0.000 claims 1
- UWAJPYAPFJCQTI-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-1-phenylmethanesulfonamide Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCCNS(=O)(=O)CC1=CC=CC=C1 UWAJPYAPFJCQTI-UHFFFAOYSA-N 0.000 claims 1
- LBDBYAMHFVCSRN-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-2,2-dimethylpropanamide Chemical compound OC1=CC(CCCNC(=O)C(C)(C)C)=CC=C1N1S(=O)(=O)NC(=O)C1 LBDBYAMHFVCSRN-UHFFFAOYSA-N 0.000 claims 1
- XSQHKHBNRJNYHH-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-2,4,6-tri(propan-2-yl)benzenesulfonamide Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1S(=O)(=O)NCCCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 XSQHKHBNRJNYHH-UHFFFAOYSA-N 0.000 claims 1
- YPIBXVFHVAEFIY-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-2,4,6-trimethylbenzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NCCCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 YPIBXVFHVAEFIY-UHFFFAOYSA-N 0.000 claims 1
- QZWOZROEZYNRHD-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-2,5-dimethylbenzenesulfonamide Chemical compound CC1=CC=C(C)C(S(=O)(=O)NCCCC=2C=C(O)C(N3S(NC(=O)C3)(=O)=O)=CC=2)=C1 QZWOZROEZYNRHD-UHFFFAOYSA-N 0.000 claims 1
- IAMABODYHWWWGJ-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-2-methylpropanamide Chemical compound OC1=CC(CCCNC(=O)C(C)C)=CC=C1N1S(=O)(=O)NC(=O)C1 IAMABODYHWWWGJ-UHFFFAOYSA-N 0.000 claims 1
- UIZQNIZUACDTPY-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-3,4-dimethoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NCCCC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 UIZQNIZUACDTPY-UHFFFAOYSA-N 0.000 claims 1
- GLLYHMNDBSUBAY-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-3,5-dimethylbenzenesulfonamide Chemical compound CC1=CC(C)=CC(S(=O)(=O)NCCCC=2C=C(O)C(N3S(NC(=O)C3)(=O)=O)=CC=2)=C1 GLLYHMNDBSUBAY-UHFFFAOYSA-N 0.000 claims 1
- POUWFXKHOKKOCB-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]-3-phenoxybenzenesulfonamide Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCCNS(=O)(=O)C(C=1)=CC=CC=1OC1=CC=CC=C1 POUWFXKHOKKOCB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- KEWWUHVSYAIVSA-UHFFFAOYSA-N 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 KEWWUHVSYAIVSA-UHFFFAOYSA-N 0.000 claims 1
- ZIIXGHQFUFEETM-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]benzenesulfonamide Chemical compound C=1C=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=1CCCNS(=O)(=O)C1=CC=CC=C1 ZIIXGHQFUFEETM-UHFFFAOYSA-N 0.000 claims 1
- DHVZUNGLFFFBFX-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]methanesulfonamide Chemical compound OC1=CC(CCCNS(=O)(=O)C)=CC=C1N1S(=O)(=O)NC(=O)C1 DHVZUNGLFFFBFX-UHFFFAOYSA-N 0.000 claims 1
- VDUSHYGJMWQHDY-UHFFFAOYSA-N n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]propanamide Chemical compound OC1=CC(CCCNC(=O)CC)=CC=C1N1S(=O)(=O)NC(=O)C1 VDUSHYGJMWQHDY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- UXXCBSVALUWLEH-UHFFFAOYSA-N n-[4-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]butyl]methanesulfonamide Chemical compound OC1=CC(CCCCNS(=O)(=O)C)=CC=C1N1S(=O)(=O)NC(=O)C1 UXXCBSVALUWLEH-UHFFFAOYSA-N 0.000 claims 1
- GVXIRCQDNGQSOA-UHFFFAOYSA-N n-[5-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]pentyl]methanesulfonamide Chemical compound OC1=CC(CCCCCNS(=O)(=O)C)=CC=C1N1S(=O)(=O)NC(=O)C1 GVXIRCQDNGQSOA-UHFFFAOYSA-N 0.000 claims 1
- UAAAOPWNJBJAQU-UHFFFAOYSA-N n-[[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]methyl]-n-methylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N(C)CC(C=C1O)=CC=C1N1CC(=O)NS1(=O)=O UAAAOPWNJBJAQU-UHFFFAOYSA-N 0.000 claims 1
- OZZBCLLLHFZLHQ-UHFFFAOYSA-N n-[[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]methyl]-n-methylmethanesulfonamide Chemical compound OC1=CC(CN(C)S(C)(=O)=O)=CC=C1N1S(=O)(=O)NC(=O)C1 OZZBCLLLHFZLHQ-UHFFFAOYSA-N 0.000 claims 1
- ULHNPPYUVHUHLR-UHFFFAOYSA-N n-ethyl-3-[[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]methyl]piperidine-1-carboxamide Chemical compound C1N(C(=O)NCC)CCCC1CC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 ULHNPPYUVHUHLR-UHFFFAOYSA-N 0.000 claims 1
- 125000004344 phenylpropyl group Chemical group 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 229940080818 propionamide Drugs 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 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 1
- GGMSGLWKIGOHLA-UHFFFAOYSA-N tert-butyl 3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-2-methylpropanoate Chemical compound OC1=CC(CC(C)C(=O)OC(C)(C)C)=CC=C1N1S(=O)(=O)NC(=O)C1 GGMSGLWKIGOHLA-UHFFFAOYSA-N 0.000 claims 1
- AQNYLFMRVJBMOO-UHFFFAOYSA-N tert-butyl 3-[[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]methyl]piperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC1CC(C=C1O)=CC=C1N1S(=O)(=O)NC(=O)C1 AQNYLFMRVJBMOO-UHFFFAOYSA-N 0.000 claims 1
- QZBSPLNCSRGMBA-UHFFFAOYSA-N tert-butyl azepane-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCCC1 QZBSPLNCSRGMBA-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 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 1
- MOXMLDDNYMMYTF-UHFFFAOYSA-N tert-butyl n-[2-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]ethyl]carbamate Chemical compound OC1=CC(CCNC(=O)OC(C)(C)C)=CC=C1N1S(=O)(=O)NC(=O)C1 MOXMLDDNYMMYTF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- SEPCHTSLRBUTRP-UHFFFAOYSA-N tert-butyl n-[3-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]propyl]carbamate Chemical compound OC1=CC(CCCNC(=O)OC(C)(C)C)=CC=C1N1S(=O)(=O)NC(=O)C1 SEPCHTSLRBUTRP-UHFFFAOYSA-N 0.000 claims 1
- FNRQBAPXQQFLLQ-UHFFFAOYSA-N tert-butyl n-[4-[3-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-2-methylbutan-2-yl]carbamate Chemical compound OC1=CC(CCC(C)(C)NC(=O)OC(C)(C)C)=CC=C1N1S(=O)(=O)NC(=O)C1 FNRQBAPXQQFLLQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
Classifications
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- 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
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
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- 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
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-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurology (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Immunology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78850206P | 2006-03-31 | 2006-03-31 | |
| US60/788,502 | 2006-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2008143053A true RU2008143053A (ru) | 2010-05-10 |
Family
ID=38458259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008143053/04A RU2008143053A (ru) | 2006-03-31 | 2007-03-29 | Тиадиазолидиноновые ингибиторы птфазы |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8084448B2 (https=) |
| EP (1) | EP2038267A2 (https=) |
| JP (1) | JP2009532379A (https=) |
| KR (1) | KR20080110882A (https=) |
| CN (1) | CN101421256A (https=) |
| AU (1) | AU2007233251A1 (https=) |
| BR (1) | BRPI0710182A2 (https=) |
| CA (1) | CA2647472A1 (https=) |
| MX (1) | MX2008012598A (https=) |
| RU (1) | RU2008143053A (https=) |
| WO (1) | WO2007115058A2 (https=) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA94921C2 (en) | 2005-12-08 | 2011-06-25 | Новартис Аг | 1-orthofluorophenyl substituted 1, 2, 5-thiazolidinedione derivatives as ptp-as inhibitors |
| CA2629819A1 (en) * | 2005-12-08 | 2007-06-14 | Novartis Ag | 1,2,5-thiazolidine derivatives useful for treating conditions mediated by protein tyrosine phosphatases (ptpase) |
| CA2630448A1 (en) * | 2005-12-08 | 2007-06-14 | Novartis Ag | 1,1,3-trioxo-1,2,5-thiadiazolidines and their use as ptp-ases inhibitors |
| UA94724C2 (en) * | 2005-12-08 | 2011-06-10 | Новартис Аг | Thiadiazolidinone derivatives as antidiabetic agents |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| AU2010327597B2 (en) * | 2009-12-04 | 2014-06-19 | Nissan Chemical Industries, Ltd. | 2-Pyridone compounds |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| JP5809157B2 (ja) * | 2010-10-08 | 2015-11-10 | 持田製薬株式会社 | 環状アミド誘導体 |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| JPWO2012147516A1 (ja) * | 2011-04-28 | 2014-07-28 | 持田製薬株式会社 | 環状アミド誘導体 |
| EP2703393A4 (en) * | 2011-04-28 | 2014-09-24 | Mochida Pharm Co Ltd | CYCLIC AMIDE DERIVATIVE |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US9216988B2 (en) * | 2011-12-22 | 2015-12-22 | Genentech, Inc. | Benzyl sulfonamide derivatives as RORc modulators |
| CN102659539A (zh) * | 2012-05-15 | 2012-09-12 | 北京化工大学 | 一种由α,β-不饱和酰氯制备二氢查尔酮类化合物的方法 |
| WO2014081718A1 (en) | 2012-11-20 | 2014-05-30 | Genentech, Inc. | Aminopyrimidine compounds as inhibitors of t790m containing egfr mutants |
| WO2017165139A1 (en) | 2016-03-25 | 2017-09-28 | St. Jude Children's Research Hospital | 1,4,5-substituted 1,2,3-triazole analogues as antagonists of the pregnane x receptor |
| AU2019200683B2 (en) * | 2018-02-01 | 2024-05-30 | The University Of Sydney | Anti-cancer compounds |
| EA202092305A1 (ru) * | 2018-03-27 | 2020-12-07 | Нейропор Терапиз, Инк. | Соединения в качестве модуляторов сигнализации tlr2 |
| BR112020026086A2 (pt) * | 2018-06-21 | 2021-03-23 | Calico Life Sciences Llc | inibidores da proteína tirosina fosfatase e métodos de uso destes |
| WO2020035019A1 (zh) | 2018-08-17 | 2020-02-20 | 浙江海正药业股份有限公司 | 吲唑胺类衍生物及其制备方法和其在医药上的用途 |
| IL286373B2 (en) * | 2019-03-14 | 2026-03-01 | Calico Life Sciences Llc | Protein tyrosine phosphate inhibitor compounds and uses thereof |
| EP4073242A4 (en) | 2019-12-12 | 2024-01-03 | Kumquat Biosciences Inc. | Compositions and methods for potentiating immune activity |
| PE20241474A1 (es) * | 2021-11-23 | 2024-07-17 | Kumquat Biosciences Inc | Compuestos que contienen heteroatomos y usos de estos |
| PE20250780A1 (es) * | 2022-02-02 | 2025-03-14 | Nerio Therapeutics Inc | Inhibidores de proteina tirosina fosfatasa y usos de estos |
| JP2025513882A (ja) * | 2022-04-14 | 2025-04-30 | ネリオ セラピューティクス，インク． | タンパク質チロシンホスファターゼ阻害剤およびその使用 |
| EP4522594A4 (en) * | 2022-05-13 | 2026-04-22 | Mondego Bio Lda A Limited Liability Company By Quotas Soc Por Quotas | PTPN2 INHIBITORS |
| CN117658947B (zh) * | 2022-09-06 | 2026-03-06 | 杭州中美华东制药有限公司 | 蛋白酪氨酸磷酸酶抑制作用的5-(取代芳基)-1,2,5-噻二唑啉-3-酮类化合物 |
| AR131413A1 (es) * | 2022-12-21 | 2025-03-19 | Bristol Myers Squibb Co | Inhibidores de la proteína tirosina fosfatasa, composiciones y métodos de uso |
| CN116283467B (zh) * | 2023-01-18 | 2024-06-11 | 四川大学 | 一种合成二芳基烷基甲烷的方法 |
| PE20252789A1 (es) | 2023-05-24 | 2025-12-22 | Kumquat Biosciences Inc | Compuestos heterociclicos y usos de estos |
| CN119818693A (zh) * | 2023-10-13 | 2025-04-15 | 华东师范大学 | 一种用于前药给药系统的可裂解支链连接体化合物及其制备和应用 |
| US20260008777A1 (en) * | 2024-07-08 | 2026-01-08 | Bristol-Myers Squibb Company | Inhibitors of protein tyrosine phosphatase, compositions, and methods of use |
| WO2026037253A1 (zh) * | 2024-08-10 | 2026-02-19 | 杭州英创医药科技有限公司 | 作为ptpn抑制剂的化合物 |
| US20260092058A1 (en) | 2024-09-30 | 2026-04-02 | St. Jude Children's Research Hospital, Inc. | Small Molecule Degraders and Fluorescent Probes of PXR |
| CN119220146A (zh) * | 2024-10-24 | 2024-12-31 | 山东三佳聚合高分子材料有限公司 | 一种新型隔热保温涂料 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2381397A (en) * | 1996-04-19 | 1997-11-12 | Novo Nordisk A/S | Modulators of molecules with phosphotyrosine recognition units |
| KR100868587B1 (ko) * | 2002-04-03 | 2008-11-12 | 노파르티스 아게 | Ｐｔｐａｓｅ 1ｂ 억제제로서의 5-치환된1,1-디옥소-1,2,5-티아졸리딘-3-온 유도체 |
| GB0225986D0 (en) * | 2002-11-07 | 2002-12-11 | Astrazeneca Ab | Chemical compounds |
| GB0227813D0 (en) * | 2002-11-29 | 2003-01-08 | Astrazeneca Ab | Chemical compounds |
| EP1594497B1 (en) * | 2002-12-30 | 2009-05-27 | Vertex Pharmaceuticals Incorporated | Sulfhydantoins as phosphate isosteres for use as phosphatase inhibitors in the treatment of cancer and autoimmune disorders |
| UA94921C2 (en) * | 2005-12-08 | 2011-06-25 | Новартис Аг | 1-orthofluorophenyl substituted 1, 2, 5-thiazolidinedione derivatives as ptp-as inhibitors |
| CA2630448A1 (en) * | 2005-12-08 | 2007-06-14 | Novartis Ag | 1,1,3-trioxo-1,2,5-thiadiazolidines and their use as ptp-ases inhibitors |
| CA2629819A1 (en) * | 2005-12-08 | 2007-06-14 | Novartis Ag | 1,2,5-thiazolidine derivatives useful for treating conditions mediated by protein tyrosine phosphatases (ptpase) |
-
2007
- 2007-03-29 CA CA002647472A patent/CA2647472A1/en not_active Abandoned
- 2007-03-29 AU AU2007233251A patent/AU2007233251A1/en not_active Abandoned
- 2007-03-29 MX MX2008012598A patent/MX2008012598A/es not_active Application Discontinuation
- 2007-03-29 CN CNA2007800120054A patent/CN101421256A/zh active Pending
- 2007-03-29 BR BRPI0710182-1A patent/BRPI0710182A2/pt not_active Application Discontinuation
- 2007-03-29 EP EP20070780835 patent/EP2038267A2/en not_active Withdrawn
- 2007-03-29 US US12/295,545 patent/US8084448B2/en not_active Expired - Fee Related
- 2007-03-29 JP JP2009503258A patent/JP2009532379A/ja active Pending
- 2007-03-29 KR KR1020087026637A patent/KR20080110882A/ko not_active Withdrawn
- 2007-03-29 RU RU2008143053/04A patent/RU2008143053A/ru not_active Application Discontinuation
- 2007-03-29 WO PCT/US2007/065421 patent/WO2007115058A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007115058A2 (en) | 2007-10-11 |
| CN101421256A (zh) | 2009-04-29 |
| WO2007115058A3 (en) | 2008-03-20 |
| US8084448B2 (en) | 2011-12-27 |
| BRPI0710182A2 (pt) | 2012-08-07 |
| KR20080110882A (ko) | 2008-12-19 |
| AU2007233251A1 (en) | 2007-10-11 |
| CA2647472A1 (en) | 2007-10-11 |
| US20090181928A1 (en) | 2009-07-16 |
| EP2038267A2 (en) | 2009-03-25 |
| MX2008012598A (es) | 2008-10-10 |
| JP2009532379A (ja) | 2009-09-10 |
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Legal Events
| Date | Code | Title | Description |
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| FA93 | Acknowledgement of application withdrawn (no request for examination) |
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