RU2008127253A - 1,1,3-триоксо-1,2,5-тиадиазолидины и их применение в качестве ингибиторов птфаз - Google Patents
1,1,3-триоксо-1,2,5-тиадиазолидины и их применение в качестве ингибиторов птфаз Download PDFInfo
- Publication number
- RU2008127253A RU2008127253A RU2008127253/04A RU2008127253A RU2008127253A RU 2008127253 A RU2008127253 A RU 2008127253A RU 2008127253/04 A RU2008127253/04 A RU 2008127253/04A RU 2008127253 A RU2008127253 A RU 2008127253A RU 2008127253 A RU2008127253 A RU 2008127253A
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- RU
- Russia
- Prior art keywords
- hydroxy
- thiadiazolidin
- dioxo
- phenyl
- trioxo
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 38
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 34
- -1 alkylthiono Chemical group 0.000 claims abstract 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 32
- 239000001257 hydrogen Substances 0.000 claims abstract 32
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 32
- 125000003118 aryl group Chemical group 0.000 claims abstract 30
- 150000003839 salts Chemical class 0.000 claims abstract 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract 23
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 22
- 229910052736 halogen Inorganic materials 0.000 claims abstract 18
- 150000002367 halogens Chemical group 0.000 claims abstract 18
- 125000004104 aryloxy group Chemical group 0.000 claims abstract 17
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract 17
- 125000001424 substituent group Chemical group 0.000 claims abstract 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract 10
- 125000004475 heteroaralkyl group Chemical group 0.000 claims abstract 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract 10
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 9
- 125000002252 acyl group Chemical group 0.000 claims abstract 7
- 125000004423 acyloxy group Chemical group 0.000 claims abstract 7
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 6
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 6
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims abstract 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 21
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 241000124008 Mammalia Species 0.000 claims 6
- 230000000694 effects Effects 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 230000001404 mediated effect Effects 0.000 claims 5
- 230000004770 neurodegeneration Effects 0.000 claims 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims 5
- 201000001320 Atherosclerosis Diseases 0.000 claims 4
- 208000032928 Dyslipidaemia Diseases 0.000 claims 4
- 208000002705 Glucose Intolerance Diseases 0.000 claims 4
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims 4
- 206010020772 Hypertension Diseases 0.000 claims 4
- 206010061218 Inflammation Diseases 0.000 claims 4
- 206010022489 Insulin Resistance Diseases 0.000 claims 4
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 208000008589 Obesity Diseases 0.000 claims 4
- 208000001132 Osteoporosis Diseases 0.000 claims 4
- 206010033645 Pancreatitis Diseases 0.000 claims 4
- 125000005110 aryl thio group Chemical group 0.000 claims 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 4
- 210000004204 blood vessel Anatomy 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 210000000987 immune system Anatomy 0.000 claims 4
- 230000004054 inflammatory process Effects 0.000 claims 4
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 4
- 208000023589 ischemic disease Diseases 0.000 claims 4
- 235000020824 obesity Nutrition 0.000 claims 4
- 208000037803 restenosis Diseases 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 230000002792 vascular Effects 0.000 claims 4
- 208000035473 Communicable disease Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 150000003573 thiols Chemical class 0.000 claims 3
- 239000005711 Benzoic acid Substances 0.000 claims 2
- 239000000883 anti-obesity agent Substances 0.000 claims 2
- 239000003472 antidiabetic agent Substances 0.000 claims 2
- 229940125708 antidiabetic agent Drugs 0.000 claims 2
- 239000002220 antihypertensive agent Substances 0.000 claims 2
- 229940030600 antihypertensive agent Drugs 0.000 claims 2
- 239000003524 antilipemic agent Substances 0.000 claims 2
- 229940125710 antiobesity agent Drugs 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
- XJMYOEAYEHXHLA-UHFFFAOYSA-N 1-ethyl-3-[3-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]phenyl]urea Chemical compound CCNC(=O)NC1=CC=CC(C=2C=C(C(O)=CC=2)N2S(NC(=O)C2)(=O)=O)=C1 XJMYOEAYEHXHLA-UHFFFAOYSA-N 0.000 claims 1
- XROPXPRFEWBBFM-UHFFFAOYSA-N 1-ethyl-3-[4-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 XROPXPRFEWBBFM-UHFFFAOYSA-N 0.000 claims 1
- BPNVRYAXIIRERG-UHFFFAOYSA-N 1-ethyl-3-[[3-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]phenyl]methyl]urea Chemical compound CCNC(=O)NCC1=CC=CC(C=2C=C(C(O)=CC=2)N2S(NC(=O)C2)(=O)=O)=C1 BPNVRYAXIIRERG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- LIALQYHGNGITJV-UHFFFAOYSA-N 2-fluoro-6-[6-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]hexoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=C(F)C=CC=C1OCCCCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 LIALQYHGNGITJV-UHFFFAOYSA-N 0.000 claims 1
- BXLNTODFUUDWLF-UHFFFAOYSA-N 2-hydroxy-6-[4-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]butoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=C(O)C=CC=C1OCCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 BXLNTODFUUDWLF-UHFFFAOYSA-N 0.000 claims 1
- YTHUKXGKIZKMOQ-UHFFFAOYSA-N 2-hydroxy-6-[5-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]pentoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=C(O)C=CC=C1OCCCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 YTHUKXGKIZKMOQ-UHFFFAOYSA-N 0.000 claims 1
- DJIQEXGQATYIDX-UHFFFAOYSA-N 2-hydroxy-6-[6-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]hexoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=C(O)C=CC=C1OCCCCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 DJIQEXGQATYIDX-UHFFFAOYSA-N 0.000 claims 1
- DJKZIRNGYFFEAT-UHFFFAOYSA-N 2-hydroxy-6-[7-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]heptoxy]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=C(O)C=CC=C1OCCCCCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 DJKZIRNGYFFEAT-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- UQVNSDDJFGRUKM-UHFFFAOYSA-N 3-[3-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]phenyl]propanenitrile Chemical compound OC1=CC=C(C=2C=C(CCC#N)C=CC=2)C=C1N1CC(=O)NS1(=O)=O UQVNSDDJFGRUKM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WNKCYMQDSUFBOG-UHFFFAOYSA-N 3-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]benzonitrile Chemical compound OC1=CC=C(C=2C=C(C=CC=2)C#N)C=C1N1CC(=O)NS1(=O)=O WNKCYMQDSUFBOG-UHFFFAOYSA-N 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
- ZNCGFDRSJASEDA-UHFFFAOYSA-N 5-(2-hydroxy-4,5-dimethylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=C(C)C(C)=CC(O)=C1N1S(=O)(=O)NC(=O)C1 ZNCGFDRSJASEDA-UHFFFAOYSA-N 0.000 claims 1
- FWDXACLZNGGLES-UHFFFAOYSA-N 5-(2-hydroxy-4-methyl-5-pentylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=C(C)C(CCCCC)=CC(N2S(NC(=O)C2)(=O)=O)=C1O FWDXACLZNGGLES-UHFFFAOYSA-N 0.000 claims 1
- HIJZVPHTDJAOEA-UHFFFAOYSA-N 5-(2-hydroxy-4-methyl-5-propylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=C(C)C(CCC)=CC(N2S(NC(=O)C2)(=O)=O)=C1O HIJZVPHTDJAOEA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- TVNNYXXPQKBCFT-UHFFFAOYSA-N 5-(2-hydroxy-5-phenylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C=2C=CC=CC=2)C=C1N1CC(=O)NS1(=O)=O TVNNYXXPQKBCFT-UHFFFAOYSA-N 0.000 claims 1
- YKOUVKCBSKVMQK-UHFFFAOYSA-N 5-(2-hydroxy-5-propoxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CCCOC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 YKOUVKCBSKVMQK-UHFFFAOYSA-N 0.000 claims 1
- CRYDVHJAQHDHTD-UHFFFAOYSA-N 5-(2-hydroxy-5-pyridin-3-ylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C=2C=NC=CC=2)C=C1N1CC(=O)NS1(=O)=O CRYDVHJAQHDHTD-UHFFFAOYSA-N 0.000 claims 1
- FINKZNUUTNUDDX-UHFFFAOYSA-N 5-(2-hydroxy-5-pyridin-4-ylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C=2C=CN=CC=2)C=C1N1CC(=O)NS1(=O)=O FINKZNUUTNUDDX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- MHSJAPZTRYZIBT-UHFFFAOYSA-N 5-(5-heptyl-2-hydroxy-4-methylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=C(C)C(CCCCCCC)=CC(N2S(NC(=O)C2)(=O)=O)=C1O MHSJAPZTRYZIBT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- NGHJOTXVBFFCSD-UHFFFAOYSA-N 5-[2-hydroxy-5-(1-methylpyrazol-4-yl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=NN(C)C=C1C1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 NGHJOTXVBFFCSD-UHFFFAOYSA-N 0.000 claims 1
- JCDQEPUEIUPLBO-UHFFFAOYSA-N 5-[2-hydroxy-5-(1-propylpyrazol-4-yl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=NN(CCC)C=C1C1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 JCDQEPUEIUPLBO-UHFFFAOYSA-N 0.000 claims 1
- UNTNDDXWVJPMJH-UHFFFAOYSA-N 5-[2-hydroxy-5-(1H-pyrazol-5-yl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C=2NN=CC=2)C=C1N1CC(=O)NS1(=O)=O UNTNDDXWVJPMJH-UHFFFAOYSA-N 0.000 claims 1
- OARCOOCXJNZTOQ-UHFFFAOYSA-N 5-[2-hydroxy-5-(1h-indol-2-yl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C=2NC3=CC=CC=C3C=2)C=C1N1CC(=O)NS1(=O)=O OARCOOCXJNZTOQ-UHFFFAOYSA-N 0.000 claims 1
- AWJCGCGVPLYIEF-UHFFFAOYSA-N 5-[2-hydroxy-5-(1h-pyrazol-4-yl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C2=CNN=C2)C=C1N1CC(=O)NS1(=O)=O AWJCGCGVPLYIEF-UHFFFAOYSA-N 0.000 claims 1
- RSUVULGQJUHZHH-UHFFFAOYSA-N 5-[2-hydroxy-5-(1h-pyrrol-2-yl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C=2NC=CC=2)C=C1N1CC(=O)NS1(=O)=O RSUVULGQJUHZHH-UHFFFAOYSA-N 0.000 claims 1
- QGBUQXALDBWMHP-UHFFFAOYSA-N 5-[2-hydroxy-5-(1h-pyrrol-3-yl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C2=CNC=C2)C=C1N1CC(=O)NS1(=O)=O QGBUQXALDBWMHP-UHFFFAOYSA-N 0.000 claims 1
- PGHMTFSDMYIZAZ-UHFFFAOYSA-N 5-[2-hydroxy-5-(2-methoxyphenyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound COC1=CC=CC=C1C1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 PGHMTFSDMYIZAZ-UHFFFAOYSA-N 0.000 claims 1
- TXCCBEAIFSJFSR-UHFFFAOYSA-N 5-[2-hydroxy-5-(2-methylphenyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC1=CC=CC=C1C1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 TXCCBEAIFSJFSR-UHFFFAOYSA-N 0.000 claims 1
- XDZSAPVJVPEQSW-UHFFFAOYSA-N 5-[2-hydroxy-5-(2-pyridin-3-ylethyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=C(N2S(NC(=O)C2)(=O)=O)C(O)=CC=C1CCC1=CC=CN=C1 XDZSAPVJVPEQSW-UHFFFAOYSA-N 0.000 claims 1
- NHFQTWSXYIZUFH-UHFFFAOYSA-N 5-[2-hydroxy-5-(3-methoxyphenyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound COC1=CC=CC(C=2C=C(C(O)=CC=2)N2S(NC(=O)C2)(=O)=O)=C1 NHFQTWSXYIZUFH-UHFFFAOYSA-N 0.000 claims 1
- AHTIBJUZODZPAV-UHFFFAOYSA-N 5-[2-hydroxy-5-(3-methylbutoxy)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC(C)CCOC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 AHTIBJUZODZPAV-UHFFFAOYSA-N 0.000 claims 1
- MHTBQVWLDIMQEH-UHFFFAOYSA-N 5-[2-hydroxy-5-(3-methylphenyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC1=CC=CC(C=2C=C(C(O)=CC=2)N2S(NC(=O)C2)(=O)=O)=C1 MHTBQVWLDIMQEH-UHFFFAOYSA-N 0.000 claims 1
- ZIKGGBPYJRUVPF-UHFFFAOYSA-N 5-[2-hydroxy-5-(4-methylpentoxy)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC(C)CCCOC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 ZIKGGBPYJRUVPF-UHFFFAOYSA-N 0.000 claims 1
- VBVYEFJLYVDXRY-UHFFFAOYSA-N 5-[2-hydroxy-5-(4-methylphenyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=CC(C)=CC=C1C1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 VBVYEFJLYVDXRY-UHFFFAOYSA-N 0.000 claims 1
- UJEKYCQVKUJFOI-UHFFFAOYSA-N 5-[2-hydroxy-5-(5-hydroxy-5-methylhexyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC(C)(O)CCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 UJEKYCQVKUJFOI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- JWWCUOWSMYIQDE-UHFFFAOYSA-N 5-[2-hydroxy-5-(6-hydroxy-6-methylheptyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC(C)(O)CCCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 JWWCUOWSMYIQDE-UHFFFAOYSA-N 0.000 claims 1
- XVEWPIJJZFXRAR-UHFFFAOYSA-N 5-[2-hydroxy-5-(6-methoxypyridin-3-yl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=NC(OC)=CC=C1C1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 XVEWPIJJZFXRAR-UHFFFAOYSA-N 0.000 claims 1
- TZPOUQZPAUBYNV-UHFFFAOYSA-N 5-[2-hydroxy-5-(7-hydroxy-6,6-dimethylheptyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OCC(C)(C)CCCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 TZPOUQZPAUBYNV-UHFFFAOYSA-N 0.000 claims 1
- PBZTUSBRPVFVAG-UHFFFAOYSA-N 5-[2-hydroxy-5-(8-hydroxy-7,7-dimethyloctyl)phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OCC(C)(C)CCCCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 PBZTUSBRPVFVAG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- LOAIYVSBPZJIHY-UHFFFAOYSA-N 5-[2-hydroxy-5-[1-(2-methylpropyl)pyrazol-4-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=NN(CC(C)C)C=C1C1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 LOAIYVSBPZJIHY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- ZSUZSVWZKXIGHB-UHFFFAOYSA-N 5-[2-hydroxy-5-[4-(hydroxymethyl)phenyl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=CC(CO)=CC=C1C1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 ZSUZSVWZKXIGHB-UHFFFAOYSA-N 0.000 claims 1
- MULKWRZKGKAZCC-UHFFFAOYSA-N 5-[2-hydroxy-5-[[(2-methoxyphenyl)methylamino]methyl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound COC1=CC=CC=C1CNCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 MULKWRZKGKAZCC-UHFFFAOYSA-N 0.000 claims 1
- OPMVADNAJTUHPU-UHFFFAOYSA-N 5-[2-hydroxy-5-[[(2-propan-2-yloxyphenyl)methylamino]methyl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC(C)OC1=CC=CC=C1CNCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 OPMVADNAJTUHPU-UHFFFAOYSA-N 0.000 claims 1
- MMZVAACGSLLXII-UHFFFAOYSA-N 5-[2-hydroxy-5-[[[2-(1-phenylpropan-2-yloxy)phenyl]methylamino]methyl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C=1C=CC=C(CNCC=2C=C(C(O)=CC=2)N2S(NC(=O)C2)(=O)=O)C=1OC(C)CC1=CC=CC=C1 MMZVAACGSLLXII-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- RDRALISQJRUENL-UHFFFAOYSA-N 5-[5-(2-cyclohexylethyl)-2-hydroxy-4-methylphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC1=CC(O)=C(N2S(NC(=O)C2)(=O)=O)C=C1CCC1CCCCC1 RDRALISQJRUENL-UHFFFAOYSA-N 0.000 claims 1
- KVILLVZEHNWSMC-UHFFFAOYSA-N 5-[5-(3,5-dimethylphenyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC1=CC(C)=CC(C=2C=C(C(O)=CC=2)N2S(NC(=O)C2)(=O)=O)=C1 KVILLVZEHNWSMC-UHFFFAOYSA-N 0.000 claims 1
- UGPNQJLVPSVLEK-UHFFFAOYSA-N 5-[5-(3-aminophenyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound NC1=CC=CC(C=2C=C(C(O)=CC=2)N2S(NC(=O)C2)(=O)=O)=C1 UGPNQJLVPSVLEK-UHFFFAOYSA-N 0.000 claims 1
- ASGPGSCUEHJZJT-UHFFFAOYSA-N 5-[5-(3-chlorophenyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C=2C=C(Cl)C=CC=2)C=C1N1CC(=O)NS1(=O)=O ASGPGSCUEHJZJT-UHFFFAOYSA-N 0.000 claims 1
- CYVDJYQITMGBFI-UHFFFAOYSA-N 5-[5-(3-fluorophenyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C=2C=C(F)C=CC=2)C=C1N1CC(=O)NS1(=O)=O CYVDJYQITMGBFI-UHFFFAOYSA-N 0.000 claims 1
- XBBKQQZCVJPZKG-UHFFFAOYSA-N 5-[5-(4-acetylphenyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 XBBKQQZCVJPZKG-UHFFFAOYSA-N 0.000 claims 1
- LNNDXRCLHLGWLC-UHFFFAOYSA-N 5-[5-(4-benzoylphenyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)C=C1N1CC(=O)NS1(=O)=O LNNDXRCLHLGWLC-UHFFFAOYSA-N 0.000 claims 1
- ALLPTHGWXLXXDW-UHFFFAOYSA-N 5-[5-(4-chlorophenyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C=2C=CC(Cl)=CC=2)C=C1N1CC(=O)NS1(=O)=O ALLPTHGWXLXXDW-UHFFFAOYSA-N 0.000 claims 1
- HCQVSUGMEUMCQO-UHFFFAOYSA-N 5-[5-(6-fluoropyridin-3-yl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C=2C=NC(F)=CC=2)C=C1N1CC(=O)NS1(=O)=O HCQVSUGMEUMCQO-UHFFFAOYSA-N 0.000 claims 1
- TYKNKCYYKSIREU-UHFFFAOYSA-N 5-[5-(butylaminomethyl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CCCCNCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 TYKNKCYYKSIREU-UHFFFAOYSA-N 0.000 claims 1
- YXVRITUHMGCOHK-UHFFFAOYSA-N 5-[5-(furan-3-yl)-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound OC1=CC=C(C2=COC=C2)C=C1N1CC(=O)NS1(=O)=O YXVRITUHMGCOHK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- BRHNPUSCBOVERJ-UHFFFAOYSA-N 5-[5-[3-(2-aminoethyl)phenyl]-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound NCCC1=CC=CC(C=2C=C(C(O)=CC=2)N2S(NC(=O)C2)(=O)=O)=C1 BRHNPUSCBOVERJ-UHFFFAOYSA-N 0.000 claims 1
- RGCVJJBUBGVJFW-UHFFFAOYSA-N 5-[5-[3-(aminomethyl)phenyl]-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound NCC1=CC=CC(C=2C=C(C(O)=CC=2)N2S(NC(=O)C2)(=O)=O)=C1 RGCVJJBUBGVJFW-UHFFFAOYSA-N 0.000 claims 1
- PSNASSCKPJMBCA-UHFFFAOYSA-N 5-[5-[[(2-ethoxyphenyl)methylamino]methyl]-2-hydroxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CCOC1=CC=CC=C1CNCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 PSNASSCKPJMBCA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- WZQPHYSUAMAABY-UHFFFAOYSA-N 7-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-2,2-dimethylheptanenitrile Chemical compound N#CC(C)(C)CCCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 WZQPHYSUAMAABY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- LLWBOGGGXKDBAY-UHFFFAOYSA-N 8-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-2,2-dimethyloctanenitrile Chemical compound N#CC(C)(C)CCCCCCC1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 LLWBOGGGXKDBAY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 239000002253 acid Substances 0.000 claims 1
- 125000005122 aminoalkylamino group Chemical group 0.000 claims 1
- 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 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 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 1
- LWLXSXXDOVPDRM-UHFFFAOYSA-N ethyl 5-[4-[4-hydroxy-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]pyrazol-1-yl]pentanoate Chemical compound C1=NN(CCCCC(=O)OCC)C=C1C1=CC=C(O)C(N2S(NC(=O)C2)(=O)=O)=C1 LWLXSXXDOVPDRM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 239000008103 glucose Substances 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 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 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 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 1
- 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 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
- 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 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000003396 thiol group Chemical class [H]S* 0.000 abstract 1
- 0 CC(*)(C=CC(*)=C1)C(O*)=C1N(CC(N1)=O)S1(=O)=O Chemical compound CC(*)(C=CC(*)=C1)C(O*)=C1N(CC(N1)=O)S1(=O)=O 0.000 description 1
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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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/433—Thidiazoles
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
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-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Immunology (AREA)
- Psychiatry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (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 |
|---|---|---|---|
| US74849305P | 2005-12-08 | 2005-12-08 | |
| US60/748,493 | 2005-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2008127253A true RU2008127253A (ru) | 2010-01-20 |
Family
ID=37807759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008127253/04A RU2008127253A (ru) | 2005-12-08 | 2006-12-06 | 1,1,3-триоксо-1,2,5-тиадиазолидины и их применение в качестве ингибиторов птфаз |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20080293782A1 (https=) |
| EP (1) | EP1960377A1 (https=) |
| JP (1) | JP2009518421A (https=) |
| KR (1) | KR20080074966A (https=) |
| CN (1) | CN101321743A (https=) |
| AU (1) | AU2006321904A1 (https=) |
| BR (1) | BRPI0619547A2 (https=) |
| CA (1) | CA2630448A1 (https=) |
| RU (1) | RU2008127253A (https=) |
| WO (1) | WO2007067614A1 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA94724C2 (en) * | 2005-12-08 | 2011-06-10 | Новартис Аг | Thiadiazolidinone derivatives as antidiabetic agents |
| 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) |
| UA94921C2 (en) | 2005-12-08 | 2011-06-25 | Новартис Аг | 1-orthofluorophenyl substituted 1, 2, 5-thiazolidinedione derivatives as ptp-as inhibitors |
| NZ569329A (en) * | 2006-01-30 | 2011-09-30 | Transtech Pharma Inc | Substituted imidazole derivatives and their use as PTPase inhibitors |
| CA2647472A1 (en) | 2006-03-31 | 2007-10-11 | Novartis Ag | Organic compounds |
| WO2008067527A1 (en) * | 2006-12-01 | 2008-06-05 | Novartis Ag | Inhibitors of protein tyrosine phosphatase for the treatment of muscle atrophy and related disorders |
| JP2011504505A (ja) * | 2007-11-21 | 2011-02-10 | デコード ジェネティクス イーエイチエフ | 肺および心血管障害を治療するためのビアリールｐｄｅ４抑制剤 |
| JP5809157B2 (ja) | 2010-10-08 | 2015-11-10 | 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 |
| JPWO2012147516A1 (ja) | 2011-04-28 | 2014-07-28 | 持田製薬株式会社 | 環状アミド誘導体 |
| CN107337635A (zh) * | 2017-07-21 | 2017-11-10 | 张家港威胜生物医药有限公司 | 一种酰胺类神经再生药物的制备方法 |
| BR112020026086A2 (pt) * | 2018-06-21 | 2021-03-23 | Calico Life Sciences Llc | inibidores da proteína tirosina fosfatase e métodos de uso destes |
| 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 |
| 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 |
| 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 |
| PE20252789A1 (es) | 2023-05-24 | 2025-12-22 | Kumquat Biosciences Inc | Compuestos heterociclicos y usos de estos |
| KR20260040037A (ko) * | 2023-07-14 | 2026-03-23 | 카톨리에케 유니버시테이트 루벤 | 암 및 대사 질병의 치료를 위한 신규 화합물 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2062558A1 (en) * | 1991-03-08 | 1992-09-09 | Prasun K. Chakravarty | Heterocyclic compounds bearing acidic functional groups as angiotensin ii antagonists |
| CA2109524A1 (en) * | 1991-05-10 | 1992-11-11 | Prasun K. Chakravarty | Acidic aralkyl triazole derivatives active as angiotensin ii antagonists |
| US5162340A (en) * | 1991-05-10 | 1992-11-10 | Merck & Co., Inc. | Substituted 1-(2h)-isoquinolinones bearing acidic functional groups as angiotensin ii antagonists |
| US5958957A (en) * | 1996-04-19 | 1999-09-28 | Novo Nordisk A/S | Modulators of molecules with phosphotyrosine recognition units |
| EP1119614B1 (en) * | 1998-07-24 | 2009-12-09 | Merck Frosst Canada Ltd. | Protein tyrosine phosphatase-1b (ptp-1b) deficient mice and uses thereof |
| 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 |
| US7141596B2 (en) * | 2003-10-08 | 2006-11-28 | Incyte Corporation | Inhibitors of proteins that bind phosphorylated molecules |
| UA94724C2 (en) * | 2005-12-08 | 2011-06-10 | Новартис Аг | Thiadiazolidinone derivatives as antidiabetic agents |
| 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) |
| UA94921C2 (en) * | 2005-12-08 | 2011-06-25 | Новартис Аг | 1-orthofluorophenyl substituted 1, 2, 5-thiazolidinedione derivatives as ptp-as inhibitors |
| CA2647472A1 (en) * | 2006-03-31 | 2007-10-11 | Novartis Ag | Organic compounds |
| CA2670491A1 (en) * | 2006-12-01 | 2008-06-12 | Novartis Ag | Inhibitors of protein tyrosine phosphatase for the promotion of physiological cardiac hypertrophy |
| AR066820A1 (es) * | 2007-06-04 | 2009-09-16 | Novartis Ag | Compuestos de tiadiazolidin-3 ona |
-
2006
- 2006-12-06 CA CA002630448A patent/CA2630448A1/en not_active Abandoned
- 2006-12-06 CN CNA2006800455922A patent/CN101321743A/zh active Pending
- 2006-12-06 JP JP2008544466A patent/JP2009518421A/ja active Pending
- 2006-12-06 KR KR1020087013698A patent/KR20080074966A/ko not_active Withdrawn
- 2006-12-06 AU AU2006321904A patent/AU2006321904A1/en not_active Abandoned
- 2006-12-06 US US12/096,421 patent/US20080293782A1/en not_active Abandoned
- 2006-12-06 WO PCT/US2006/046544 patent/WO2007067614A1/en not_active Ceased
- 2006-12-06 RU RU2008127253/04A patent/RU2008127253A/ru not_active Application Discontinuation
- 2006-12-06 BR BRPI0619547-4A patent/BRPI0619547A2/pt not_active IP Right Cessation
- 2006-12-06 EP EP06839093A patent/EP1960377A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US20080293782A1 (en) | 2008-11-27 |
| AU2006321904A8 (en) | 2008-07-17 |
| BRPI0619547A2 (pt) | 2011-10-04 |
| JP2009518421A (ja) | 2009-05-07 |
| AU2006321904A1 (en) | 2007-06-14 |
| WO2007067614A1 (en) | 2007-06-14 |
| KR20080074966A (ko) | 2008-08-13 |
| CA2630448A1 (en) | 2007-06-14 |
| EP1960377A1 (en) | 2008-08-27 |
| CN101321743A (zh) | 2008-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20110202 |