ZA200202063B - Benzylidene-thiazolidinediones and analogues and their use in the treatment of inflammation. - Google Patents
Benzylidene-thiazolidinediones and analogues and their use in the treatment of inflammation. Download PDFInfo
- Publication number
- ZA200202063B ZA200202063B ZA200202063A ZA200202063A ZA200202063B ZA 200202063 B ZA200202063 B ZA 200202063B ZA 200202063 A ZA200202063 A ZA 200202063A ZA 200202063 A ZA200202063 A ZA 200202063A ZA 200202063 B ZA200202063 B ZA 200202063B
- Authority
- ZA
- South Africa
- Prior art keywords
- substituted
- thiazolidinedione
- tetrahydro
- naphthyl
- pentamethyl
- Prior art date
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- 230000004054 inflammatory process Effects 0.000 title description 9
- SGIZECXZFLAGBW-UHFFFAOYSA-N 5-benzylidene-1,3-thiazolidine-2,4-dione Chemical class S1C(=O)NC(=O)C1=CC1=CC=CC=C1 SGIZECXZFLAGBW-UHFFFAOYSA-N 0.000 title description 7
- 206010061218 Inflammation Diseases 0.000 title description 7
- -1 nitro, hydroxyl Chemical group 0.000 claims description 263
- 150000001875 compounds Chemical class 0.000 claims description 161
- 125000000217 alkyl group Chemical group 0.000 claims description 80
- 229940123464 Thiazolidinedione Drugs 0.000 claims description 79
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 75
- 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 75
- 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 73
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 68
- 125000003545 alkoxy group Chemical group 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 57
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 55
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 51
- 229910052736 halogen Inorganic materials 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 150000002367 halogens Chemical class 0.000 claims description 48
- 125000001188 haloalkyl group Chemical group 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- 125000003342 alkenyl group Chemical group 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 37
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 35
- 125000004423 acyloxy group Chemical group 0.000 claims description 33
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- 125000000304 alkynyl group Chemical group 0.000 claims description 30
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000004001 thioalkyl group Chemical group 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 21
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 20
- 230000037356 lipid metabolism Effects 0.000 claims description 20
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 17
- 206010028980 Neoplasm Diseases 0.000 claims description 15
- 238000005859 coupling reaction Methods 0.000 claims description 14
- 201000011510 cancer Diseases 0.000 claims description 13
- 230000023852 carbohydrate metabolic process Effects 0.000 claims description 12
- 235000021256 carbohydrate metabolism Nutrition 0.000 claims description 12
- 150000002632 lipids Chemical class 0.000 claims description 11
- MJAMNJNCEOHYIU-UHFFFAOYSA-N 1,2-oxazolidine-3,4-dione Chemical compound O=C1CONC1=O MJAMNJNCEOHYIU-UHFFFAOYSA-N 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 238000010168 coupling process Methods 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 208000027866 inflammatory disease Diseases 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 201000009030 Carcinoma Diseases 0.000 claims description 4
- 208000011231 Crohn disease Diseases 0.000 claims description 4
- 230000004663 cell proliferation Effects 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 208000032839 leukemia Diseases 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- JOWCRAWAGHINBQ-UHFFFAOYSA-N 3-[[4-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)-3-(trifluoromethoxy)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(C(=C1)OC(F)(F)F)=CC=C1CN1C(=O)CSC1=O JOWCRAWAGHINBQ-UHFFFAOYSA-N 0.000 claims description 3
- MPSJOSNIUNDKJB-UHFFFAOYSA-N 5-[[2-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)-3-propan-2-yloxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(C(CCC2(C)C)(C)C)=C2C=C(C)C=1C=1C(OC(C)C)=CC=CC=1C=C1SC(=O)NC1=O MPSJOSNIUNDKJB-UHFFFAOYSA-N 0.000 claims description 3
- SXRDKRSLYBTRFH-UHFFFAOYSA-N 5-[[3-hydroxy-2-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C1=C(O)C=CC=C1C=C1SC(=O)NC1=O SXRDKRSLYBTRFH-UHFFFAOYSA-N 0.000 claims description 3
- UONHUEWDGOSXTK-UHFFFAOYSA-N 5-[[3-methoxy-2-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(C(CCC2(C)C)(C)C)=C2C=C(C)C=1C=1C(OC)=CC=CC=1C=C1SC(=O)NC1=O UONHUEWDGOSXTK-UHFFFAOYSA-N 0.000 claims description 3
- 206010006187 Breast cancer Diseases 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
- 206010009944 Colon cancer Diseases 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 206010025323 Lymphomas Diseases 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 208000029742 colonic neoplasm Diseases 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- YDKLYEJKPBVZQC-UHFFFAOYSA-N n-[3-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]acetamide Chemical compound C=1C(C(CCC2(C)C)(C)C)=C2C=C(C)C=1C=1C(NC(=O)C)=CC=CC=1C=C1SC(=O)NC1=O YDKLYEJKPBVZQC-UHFFFAOYSA-N 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- GFMGTUPCQRJBNU-UHFFFAOYSA-N 3-[[2-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)-3-(trifluoromethoxy)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(C(=CC=C1)OC(F)(F)F)=C1CN1C(=O)CSC1=O GFMGTUPCQRJBNU-UHFFFAOYSA-N 0.000 claims description 2
- KKKMOENKDVEBPK-UHFFFAOYSA-N 3-[[2-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)-3-(trifluoromethyl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(C(=CC=C1)C(F)(F)F)=C1CN1C(=O)CSC1=O KKKMOENKDVEBPK-UHFFFAOYSA-N 0.000 claims description 2
- UTLQJDCMVOPUTP-UHFFFAOYSA-N 3-[[2-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)-3-propan-2-yloxyphenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(C(CCC2(C)C)(C)C)=C2C=C(C)C=1C=1C(OC(C)C)=CC=CC=1CN1C(=O)CSC1=O UTLQJDCMVOPUTP-UHFFFAOYSA-N 0.000 claims description 2
- JHHKLVZEYKSCIZ-UHFFFAOYSA-N 3-[[2-(3-methoxy-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-3-(trifluoromethoxy)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound COC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(C(=CC=C1)OC(F)(F)F)=C1CN1C(=O)CSC1=O JHHKLVZEYKSCIZ-UHFFFAOYSA-N 0.000 claims description 2
- LHXQUOUYPZTYFJ-UHFFFAOYSA-N 3-[[2-[3-(dimethylamino)-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl]-3-(trifluoromethoxy)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CN(C)C1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(C(=CC=C1)OC(F)(F)F)=C1CN1C(=O)CSC1=O LHXQUOUYPZTYFJ-UHFFFAOYSA-N 0.000 claims description 2
- KEHBQQWGRNEXQY-UHFFFAOYSA-N 3-[[2-fluoro-3-methoxy-4-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=C(C=2C(=CC3=C(C(CCC3(C)C)(C)C)C=2)C)C(OC)=C(F)C=1CN1C(=O)CSC1=O KEHBQQWGRNEXQY-UHFFFAOYSA-N 0.000 claims description 2
- NRYRYJSPDFNWGB-UHFFFAOYSA-N 3-[[3-(dimethylamino)-2-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(C(CCC2(C)C)(C)C)=C2C=C(C)C=1C=1C(N(C)C)=CC=CC=1CN1C(=O)CSC1=O NRYRYJSPDFNWGB-UHFFFAOYSA-N 0.000 claims description 2
- WBDNROMTGTXBSB-UHFFFAOYSA-N 3-[[3-(dimethylamino)-4-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=C(C=2C(=CC3=C(C(CCC3(C)C)(C)C)C=2)C)C(N(C)C)=CC=1CN1C(=O)CSC1=O WBDNROMTGTXBSB-UHFFFAOYSA-N 0.000 claims description 2
- WWQPFJVWIZNWER-UHFFFAOYSA-N 3-[[3-(dimethylamino)-4-[5,5,8,8-tetramethyl-3-(trifluoromethyl)-6,7-dihydronaphthalen-2-yl]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=C(C=2C(=CC3=C(C(CCC3(C)C)(C)C)C=2)C(F)(F)F)C(N(C)C)=CC=1CN1C(=O)CSC1=O WWQPFJVWIZNWER-UHFFFAOYSA-N 0.000 claims description 2
- BIPSWKLBVNHAIS-UHFFFAOYSA-N 3-[[3-amino-4-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(C(=C1)N)=CC=C1CN1C(=O)CSC1=O BIPSWKLBVNHAIS-UHFFFAOYSA-N 0.000 claims description 2
- UVKIROKGUFONEF-UHFFFAOYSA-N 3-[[3-chloro-2-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C1=C(Cl)C=CC=C1CN1C(=O)CSC1=O UVKIROKGUFONEF-UHFFFAOYSA-N 0.000 claims description 2
- VSNXCHKTRSUVOE-UHFFFAOYSA-N 3-[[3-chloro-4-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(C(=C1)Cl)=CC=C1CN1C(=O)CSC1=O VSNXCHKTRSUVOE-UHFFFAOYSA-N 0.000 claims description 2
- CJFUQGURHBQRRI-UHFFFAOYSA-N 3-[[3-ethyl-2-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(C(CCC2(C)C)(C)C)=C2C=C(C)C=1C=1C(CC)=CC=CC=1CN1C(=O)CSC1=O CJFUQGURHBQRRI-UHFFFAOYSA-N 0.000 claims description 2
- OAIYTBLIAZVCAB-UHFFFAOYSA-N 3-[[3-ethyl-4-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=C(C=2C(=CC3=C(C(CCC3(C)C)(C)C)C=2)C)C(CC)=CC=1CN1C(=O)CSC1=O OAIYTBLIAZVCAB-UHFFFAOYSA-N 0.000 claims description 2
- YGPSEFGOGGXUHJ-UHFFFAOYSA-N 3-[[3-fluoro-5-methoxy-4-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(F)=C(C=2C(=CC3=C(C(CCC3(C)C)(C)C)C=2)C)C(OC)=CC=1CN1C(=O)CSC1=O YGPSEFGOGGXUHJ-UHFFFAOYSA-N 0.000 claims description 2
- UMVFUVYECIZZQL-UHFFFAOYSA-N 3-[[3-hydroxy-2-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C1=C(O)C=CC=C1CN1C(=O)CSC1=O UMVFUVYECIZZQL-UHFFFAOYSA-N 0.000 claims description 2
- JRBNWBKLLGFOCX-UHFFFAOYSA-N 3-[[3-hydroxy-4-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(C(=C1)O)=CC=C1CN1C(=O)CSC1=O JRBNWBKLLGFOCX-UHFFFAOYSA-N 0.000 claims description 2
- KKAUIMBNTXAOKP-UHFFFAOYSA-N 3-[[3-methoxy-2-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(C(CCC2(C)C)(C)C)=C2C=C(C)C=1C=1C(OC)=CC=CC=1CN1C(=O)CSC1=O KKAUIMBNTXAOKP-UHFFFAOYSA-N 0.000 claims description 2
- YUPWQCWCRASOAL-UHFFFAOYSA-N 3-[[3-methoxy-2-[5,5,8,8-tetramethyl-3-(trifluoromethyl)-6,7-dihydronaphthalen-2-yl]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(C(CCC2(C)C)(C)C)=C2C=C(C(F)(F)F)C=1C=1C(OC)=CC=CC=1CN1C(=O)CSC1=O YUPWQCWCRASOAL-UHFFFAOYSA-N 0.000 claims description 2
- CVNKLYWOENBNRY-UHFFFAOYSA-N 3-[[3-methoxy-4-[5,5,8,8-tetramethyl-3-(trifluoromethyl)-6,7-dihydronaphthalen-2-yl]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=C(C=2C(=CC3=C(C(CCC3(C)C)(C)C)C=2)C(F)(F)F)C(OC)=CC=1CN1C(=O)CSC1=O CVNKLYWOENBNRY-UHFFFAOYSA-N 0.000 claims description 2
- JHMYELCJZRBRHY-UHFFFAOYSA-N 3-[[3-methyl-2-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(C(CCC2(C)C)(C)C)=C2C=C(C)C=1C=1C(C)=CC=CC=1CN1C(=O)CSC1=O JHMYELCJZRBRHY-UHFFFAOYSA-N 0.000 claims description 2
- PZYXNZNDSUQZSL-UHFFFAOYSA-N 3-[[3-methyl-4-[5,5,8,8-tetramethyl-3-(trifluoromethyl)-6,7-dihydronaphthalen-2-yl]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=C(C=2C(=CC3=C(C(CCC3(C)C)(C)C)C=2)C(F)(F)F)C(C)=CC=1CN1C(=O)CSC1=O PZYXNZNDSUQZSL-UHFFFAOYSA-N 0.000 claims description 2
- JJSORLAXOUSVGT-UHFFFAOYSA-N 3-[[4-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)-3-(trifluoromethyl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(C(=C1)C(F)(F)F)=CC=C1CN1C(=O)CSC1=O JJSORLAXOUSVGT-UHFFFAOYSA-N 0.000 claims description 2
- ADLJGKIMXRNPKY-UHFFFAOYSA-N 3-[[4-(3-methoxy-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-3-(trifluoromethoxy)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound COC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(C(=C1)OC(F)(F)F)=CC=C1CN1C(=O)CSC1=O ADLJGKIMXRNPKY-UHFFFAOYSA-N 0.000 claims description 2
- XVOQORQHPRZDKD-UHFFFAOYSA-N 3-[[4-[3-(dimethylamino)-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl]-3-(trifluoromethoxy)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CN(C)C1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(C(=C1)OC(F)(F)F)=CC=C1CN1C(=O)CSC1=O XVOQORQHPRZDKD-UHFFFAOYSA-N 0.000 claims description 2
- BLNPYGYDJOEBJE-UHFFFAOYSA-N 3-[[4-ethoxy-4-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)cyclohexa-1,5-dien-1-yl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1=CC(OCC)(C=2C(=CC3=C(C(CCC3(C)C)(C)C)C=2)C)CC=C1CN1C(=O)CSC1=O BLNPYGYDJOEBJE-UHFFFAOYSA-N 0.000 claims description 2
- GSPCNFCODZZIEZ-UHFFFAOYSA-N 3-[[4-fluoro-3-methoxy-2-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(C(CCC2(C)C)(C)C)=C2C=C(C)C=1C=1C(OC)=C(F)C=CC=1CN1C(=O)CSC1=O GSPCNFCODZZIEZ-UHFFFAOYSA-N 0.000 claims description 2
- NEXYEDCIXGILLF-UHFFFAOYSA-N 3-[[6-fluoro-3-methoxy-2-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(C(CCC2(C)C)(C)C)=C2C=C(C)C=1C=1C(OC)=CC=C(F)C=1CN1C(=O)CSC1=O NEXYEDCIXGILLF-UHFFFAOYSA-N 0.000 claims description 2
- KYYFRVZHULJLBV-UHFFFAOYSA-N 5-[[2-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)-3-(trifluoromethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C1=C(OC(F)(F)F)C=CC=C1C=C1SC(=O)NC1=O KYYFRVZHULJLBV-UHFFFAOYSA-N 0.000 claims description 2
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ATE310733T1 (de) * | 2000-04-21 | 2005-12-15 | Pfizer Prod Inc | Thyroid-rezeptorliganden |
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CA2340824A1 (en) * | 2001-03-14 | 2002-09-14 | Ibm Canada Limited-Ibm Canada Limitee | Method and system for application behavior analysis |
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ATE442148T1 (de) | 2001-04-04 | 2009-09-15 | Ortho Mcneil Janssen Pharm | Kombinationstherapie durch glukoseresorptionshemmer und retinoid x rezeptorenmodulatoren |
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FR2845384B1 (fr) * | 2002-10-04 | 2004-12-31 | Fournier Lab Sa | Composes derives de la 2-thiohydantoine et leur utilisation en therapeutique |
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JP2006523724A (ja) * | 2003-04-18 | 2006-10-19 | インサイト サン ディエゴ インコーポレイテッド | 代謝障害、癌および他の疾患の治療のための置換イソクロマン化合物 |
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CA2549017A1 (en) | 2003-08-01 | 2005-02-10 | Mona Patel | Substituted indazole-o-glucosides |
CA2549015A1 (en) | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica N.V. | Substituted fused heterocyclic c-glycosides |
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DE102008022221A1 (de) * | 2008-05-06 | 2009-11-12 | Universität des Saarlandes | Inhibitoren der humanen Aldosteronsynthase CYP11B2 |
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CA2777406A1 (en) | 2009-10-09 | 2011-04-14 | The Ohio State University Research Foundation | Thiazolidinedione energy restriction-mimetic agents |
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CN102432544B (zh) * | 2011-11-17 | 2014-05-21 | 天津医科大学 | 5-取代苄亚甲基咪唑烷-2,4-二酮类衍生物及其应用 |
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MA54133B1 (fr) | 2018-03-08 | 2022-01-31 | Incyte Corp | Composés d'aminopyrazine diol utilisés comme inhibiteurs de pi3k-y |
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2000
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- 2000-08-31 EP EP00961550A patent/EP1214305A1/en not_active Withdrawn
- 2000-08-31 CA CA002384194A patent/CA2384194A1/en not_active Abandoned
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