KR20080094806A - 치환된 이미다졸 유도체 및 이의 ＰＴＰａｓｅ 억제제로서의 용도 - Google Patents
치환된 이미다졸 유도체 및 이의 ＰＴＰａｓｅ 억제제로서의 용도 Download PDFInfo
- Publication number
- KR20080094806A KR20080094806A KR1020087021180A KR20087021180A KR20080094806A KR 20080094806 A KR20080094806 A KR 20080094806A KR 1020087021180 A KR1020087021180 A KR 1020087021180A KR 20087021180 A KR20087021180 A KR 20087021180A KR 20080094806 A KR20080094806 A KR 20080094806A
- Authority
- KR
- South Korea
- Prior art keywords
- phenyl
- alkyl
- compound
- dichloro
- alkylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 102000002727 Protein Tyrosine Phosphatase Human genes 0.000 title claims abstract description 37
- 108020000494 protein-tyrosine phosphatase Proteins 0.000 title claims abstract description 37
- 239000003112 inhibitor Substances 0.000 title claims description 14
- 150000002460 imidazoles Chemical class 0.000 title abstract description 7
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 390
- 150000001875 compounds Chemical class 0.000 claims abstract description 213
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 34
- 201000010099 disease Diseases 0.000 claims abstract description 29
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 23
- 230000001404 mediated effect Effects 0.000 claims abstract description 11
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 11
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims abstract description 9
- -1 4,5-diaza-indanyl Chemical group 0.000 claims description 293
- 125000000217 alkyl group Chemical group 0.000 claims description 223
- 239000000203 mixture Substances 0.000 claims description 98
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 97
- 239000001257 hydrogen Substances 0.000 claims description 74
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 229910052757 nitrogen Inorganic materials 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 229910052799 carbon Inorganic materials 0.000 claims description 55
- 229910005965 SO 2 Inorganic materials 0.000 claims description 50
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims description 39
- 125000002947 alkylene group Chemical group 0.000 claims description 37
- 125000000304 alkynyl group Chemical group 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 229910052721 tungsten Inorganic materials 0.000 claims description 29
- 229910052727 yttrium Inorganic materials 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 125000001188 haloalkyl group Chemical group 0.000 claims description 19
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000004450 alkenylene group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 16
- 239000003937 drug carrier Substances 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
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- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 208000026278 immune system disease Diseases 0.000 claims description 11
- 150000002500 ions Chemical class 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000000122 growth hormone Substances 0.000 claims description 10
- 102000018997 Growth Hormone Human genes 0.000 claims description 9
- 108010051696 Growth Hormone Proteins 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 229940124597 therapeutic agent Drugs 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000011593 sulfur Chemical group 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
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- 125000004429 atom Chemical group 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
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- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 claims description 6
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims description 6
- 102000004877 Insulin Human genes 0.000 claims description 6
- 108090001061 Insulin Proteins 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000556 agonist Substances 0.000 claims description 6
- 125000005275 alkylenearyl group Chemical group 0.000 claims description 6
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims description 6
- 125000004419 alkynylene group Chemical group 0.000 claims description 6
- 239000003102 growth factor Substances 0.000 claims description 6
- 229940125396 insulin Drugs 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 229940088597 hormone Drugs 0.000 claims description 5
- 239000005556 hormone Substances 0.000 claims description 5
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 5
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 5
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 5
- TXYJDNWZUTXIEW-UHFFFAOYSA-N 5-[3-[2-[[4-[3-(2-cyclohexylethylsulfanyl)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound ClC1=CC(Cl)=CC=C1C1=CN(C=2C=C(C=CC=2)N2S(NC(=O)C2)(=O)=O)C(CC=2C=CC(=CC=2)C=2C=C(SCCC3CCCCC3)C=CC=2)=N1 TXYJDNWZUTXIEW-UHFFFAOYSA-N 0.000 claims description 4
- UFYGBSOSGMSRFG-UHFFFAOYSA-N 5-[3-[2-[[4-[3-(cyclohexylmethylsulfanyl)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound ClC1=CC(Cl)=CC=C1C1=CN(C=2C=C(C=CC=2)N2S(NC(=O)C2)(=O)=O)C(CC=2C=CC(=CC=2)C=2C=C(SCC3CCCCC3)C=CC=2)=N1 UFYGBSOSGMSRFG-UHFFFAOYSA-N 0.000 claims description 4
- AUIVFJGHRNVUJX-UHFFFAOYSA-N 5-[3-[4-(2,4-difluorophenyl)-2-[[4-[3-(3,3-dimethylbutylsulfanyl)phenyl]phenyl]methyl]imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC(C)(C)CCSC1=CC=CC(C=2C=CC(CC=3N(C=C(N=3)C=3C(=CC(F)=CC=3)F)C=3C=C(C=CC=3)N3S(NC(=O)C3)(=O)=O)=CC=2)=C1 AUIVFJGHRNVUJX-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims description 3
- BHLLGPUOHKTNMM-UHFFFAOYSA-N 5-[3-[2-[[4-[4-(cyclohexylmethylsulfanyl)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound ClC1=CC(Cl)=CC=C1C1=CN(C=2C=C(C=CC=2)N2S(NC(=O)C2)(=O)=O)C(CC=2C=CC(=CC=2)C=2C=CC(SCC3CCCCC3)=CC=2)=N1 BHLLGPUOHKTNMM-UHFFFAOYSA-N 0.000 claims description 3
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- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 claims description 3
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- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 3
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- OQTHCHRSZIOATC-UHFFFAOYSA-N 5-[3-[2-[[4-(4-cyclohexylphenyl)phenyl]methyl]-4-(2,6-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound ClC1=CC=CC(Cl)=C1C1=CN(C=2C=C(C=CC=2)N2S(NC(=O)C2)(=O)=O)C(CC=2C=CC(=CC=2)C=2C=CC(=CC=2)C2CCCCC2)=N1 OQTHCHRSZIOATC-UHFFFAOYSA-N 0.000 claims description 2
- FDJREESJACNDKJ-UHFFFAOYSA-N 5-[3-[2-[[4-[3-(2-cyclohexylethoxy)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound ClC1=CC(Cl)=CC=C1C1=CN(C=2C=C(C=CC=2)N2S(NC(=O)C2)(=O)=O)C(CC=2C=CC(=CC=2)C=2C=C(OCCC3CCCCC3)C=CC=2)=N1 FDJREESJACNDKJ-UHFFFAOYSA-N 0.000 claims description 2
- UKRPUOPDTNRJGU-UHFFFAOYSA-N 5-[3-[2-[[4-[3-(cyclohexylmethoxy)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound ClC1=CC(Cl)=CC=C1C1=CN(C=2C=C(C=CC=2)N2S(NC(=O)C2)(=O)=O)C(CC=2C=CC(=CC=2)C=2C=C(OCC3CCCCC3)C=CC=2)=N1 UKRPUOPDTNRJGU-UHFFFAOYSA-N 0.000 claims description 2
- VZWHFHHFCFNSAG-UHFFFAOYSA-N 5-[3-[2-[[4-[3-(cyclohexylmethoxy)phenyl]phenyl]methyl]-4-(2,6-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound ClC1=CC=CC(Cl)=C1C1=CN(C=2C=C(C=CC=2)N2S(NC(=O)C2)(=O)=O)C(CC=2C=CC(=CC=2)C=2C=C(OCC3CCCCC3)C=CC=2)=N1 VZWHFHHFCFNSAG-UHFFFAOYSA-N 0.000 claims description 2
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- MMXCNGUFTHHIBA-UHFFFAOYSA-N methyl 2-[4-[2-[[4-(4-butan-2-ylphenyl)phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]anilino]acetate Chemical compound C1=CC(C(C)CC)=CC=C1C(C=C1)=CC=C1CC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CN1C1=CC=C(NCC(=O)OC)C=C1 MMXCNGUFTHHIBA-UHFFFAOYSA-N 0.000 description 2
- TXWKHORQOBMSQC-UHFFFAOYSA-N methyl 2-[4-[2-[[4-(4-cyclohexylphenyl)phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]anilino]acetate Chemical compound C1=CC(NCC(=O)OC)=CC=C1N1C(CC=2C=CC(=CC=2)C=2C=CC(=CC=2)C2CCCCC2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 TXWKHORQOBMSQC-UHFFFAOYSA-N 0.000 description 2
- NURTVXGLMVLMBR-UHFFFAOYSA-N methyl 2-[4-[2-[[4-(4-cyclohexylphenyl)phenyl]methyl]-4-(4-methylsulfonylphenyl)imidazol-1-yl]anilino]acetate Chemical compound C1=CC(NCC(=O)OC)=CC=C1N1C(CC=2C=CC(=CC=2)C=2C=CC(=CC=2)C2CCCCC2)=NC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1 NURTVXGLMVLMBR-UHFFFAOYSA-N 0.000 description 2
- XJWWZJPJUCGFHD-UHFFFAOYSA-N methyl 2-[4-[2-[[4-(4-cyclohexylphenyl)phenyl]methyl]-4-[4-(trifluoromethyl)phenyl]imidazol-1-yl]anilino]acetate Chemical compound C1=CC(NCC(=O)OC)=CC=C1N1C(CC=2C=CC(=CC=2)C=2C=CC(=CC=2)C2CCCCC2)=NC(C=2C=CC(=CC=2)C(F)(F)F)=C1 XJWWZJPJUCGFHD-UHFFFAOYSA-N 0.000 description 2
- CITOVJRBBKTNKH-UHFFFAOYSA-N methyl 2-[4-[2-[[6-(cyclohexylmethoxy)naphthalen-2-yl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]anilino]acetate Chemical compound C1=CC(NCC(=O)OC)=CC=C1N1C(CC=2C=C3C=CC(OCC4CCCCC4)=CC3=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 CITOVJRBBKTNKH-UHFFFAOYSA-N 0.000 description 2
- NKNASKIKBCDNHM-UHFFFAOYSA-N methyl 2-[4-[4-(2,4-dichlorophenyl)-2-[(6-methoxynaphthalen-2-yl)methyl]imidazol-1-yl]anilino]acetate Chemical compound C1=CC(NCC(=O)OC)=CC=C1N1C(CC=2C=C3C=CC(OC)=CC3=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 NKNASKIKBCDNHM-UHFFFAOYSA-N 0.000 description 2
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- JPCPOZMHGHZFKN-UHFFFAOYSA-N methyl 2-[4-[4-(2,4-dichlorophenyl)-2-[[4-[4-(3,3-dimethylbutoxy)phenyl]phenyl]methyl]imidazol-1-yl]anilino]acetate Chemical compound C1=CC(NCC(=O)OC)=CC=C1N1C(CC=2C=CC(=CC=2)C=2C=CC(OCCC(C)(C)C)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 JPCPOZMHGHZFKN-UHFFFAOYSA-N 0.000 description 2
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- 229910052722 tritium Chemical group 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
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- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
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- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- 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
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- Hospice & Palliative Care (AREA)
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| US76325606P | 2006-01-30 | 2006-01-30 | |
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| JP4898458B2 (ja) * | 2004-02-12 | 2012-03-14 | トランス テック ファーマ，インコーポレイテッド | 置換アゾール誘導体、組成物及び使用方法 |
| BRPI0707338A2 (pt) * | 2006-01-30 | 2011-05-03 | Transtech Pharma Inc | derivados de imidazol, composições, e métodos substituìdos de uso como inibidores de ptpase |
| EP2438059A1 (en) | 2009-06-05 | 2012-04-11 | Link Medicine Corporation | Aminopyrrolidinone derivatives and uses thereof |
| JPWO2011007819A1 (ja) | 2009-07-17 | 2012-12-27 | 塩野義製薬株式会社 | ラクタムまたはベンゼンスルホンアミド化合物を含有する医薬 |
| JP5398076B2 (ja) * | 2009-12-10 | 2014-01-29 | 四国化成工業株式会社 | ２−（ブロモベンジル）−４−（ブロモフェニル）−５−メチルイミダゾール化合物 |
| JP5398075B2 (ja) * | 2010-01-13 | 2014-01-29 | 四国化成工業株式会社 | ４−（ジクロロフェニル）−２−（４−フルオロベンジル）−５−メチルイミダゾール化合物 |
| RU2013114390A (ru) | 2010-08-31 | 2014-10-10 | СНУ Ар энд ДиБи ФАУНДЕЙШН | Применение фетального репрограммирования посредством ppar-дельта-агониста |
| JP5809157B2 (ja) | 2010-10-08 | 2015-11-10 | 持田製薬株式会社 | 環状アミド誘導体 |
| WO2012094580A2 (en) | 2011-01-07 | 2012-07-12 | High Point Pharmaceuticals, Llc | Compounds that modulate oxidative stress |
| AU2012248627A1 (en) | 2011-04-28 | 2013-11-14 | Mochida Pharmaceutical Co., Ltd. | Cyclic amide derivative |
| EP3353156B1 (en) | 2015-09-23 | 2021-11-03 | The General Hospital Corporation | Tead transcription factor autopalmitoylation inhibitors |
| KR102667386B1 (ko) | 2015-10-07 | 2024-05-21 | 미토브리지, 인크. | Ppar 효능제, 화합물, 제약 조성물, 및 그의 사용 방법 |
| BR112018069930B1 (pt) * | 2016-04-13 | 2024-02-20 | Mitobridge, Inc | Compostos agonistas de ppar, uso dos mesmos e composição farmacêutica |
| EA202092441A1 (ru) | 2016-06-07 | 2021-05-21 | Джакобио Фармасьютикалс Ко., Лтд. | Новые гетероциклические производные, применимые в качестве ингибиторов shp2 |
| KR20240026521A (ko) | 2017-03-23 | 2024-02-28 | 자코바이오 파마슈티칼스 컴퍼니 리미티드 | Shp2 억제제로서 유용한 신규한 헤테로환형 유도체 |
| KR20250133466A (ko) * | 2018-06-21 | 2025-09-05 | 칼리코 라이프 사이언시스 엘엘씨 | 단백질 타이로신 포스파타아제 억제제 및 그의 사용 방법 |
| CN112839935A (zh) | 2018-09-26 | 2021-05-25 | 北京加科思新药研发有限公司 | 可用作shp2抑制剂的新型杂环衍生物 |
| EP3937943A4 (en) | 2019-03-15 | 2022-12-07 | The General Hospital Corporation | NEW SMALL MOLECULE INHIBITORS OF TEAD TRANSCRIPTION FACTORS |
| US11058695B2 (en) * | 2019-11-08 | 2021-07-13 | Myongji University Industry And Academia Cooperation Foundation | Inhibitor of carbapenem-hydrolyzing class D beta-lactamases |
| WO2022035805A1 (en) * | 2020-08-10 | 2022-02-17 | Dana-Farber Cancer Institute, Inc. | Substituted 1,2,4-oxadiazoles as small molecule inhibitors of ubiquitin-specific protease 28 |
| ES2999626T3 (en) * | 2020-10-09 | 2025-02-26 | Bristol Myers Squibb Co | Aminoimidazole fpr2 agonists |
| EP4227299A4 (en) * | 2020-10-12 | 2025-04-09 | Hangzhou Zhongmeihuadong Pharmaceutical Co., Ltd. | GLP-1 RECEPTOR AGONIST, BENZIMIDAZOLONE AND ITS USE |
| 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 |
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2007
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- 2007-01-30 EA EA200870218A patent/EA019385B1/ru not_active IP Right Cessation
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| IL192557A (en) | 2013-09-30 |
| US20070191385A1 (en) | 2007-08-16 |
| HK1127342A1 (en) | 2009-09-25 |
| IL192557A0 (en) | 2009-02-11 |
| JP2009525340A (ja) | 2009-07-09 |
| JP5180099B2 (ja) | 2013-04-10 |
| EP1991544B1 (en) | 2018-08-15 |
| US7723369B2 (en) | 2010-05-25 |
| BRPI0707338A2 (pt) | 2011-05-03 |
| CA2637024A1 (en) | 2007-08-09 |
| US8404731B2 (en) | 2013-03-26 |
| ZA200805648B (en) | 2009-09-30 |
| CN101374835B (zh) | 2012-04-25 |
| AU2007211319A1 (en) | 2007-08-09 |
| US20100113331A1 (en) | 2010-05-06 |
| WO2007089857A3 (en) | 2008-06-26 |
| CN101374835A (zh) | 2009-02-25 |
| EP1991544A2 (en) | 2008-11-19 |
| CA2637024C (en) | 2013-05-14 |
| WO2007089857A2 (en) | 2007-08-09 |
| NZ569329A (en) | 2011-09-30 |
| US20120196906A1 (en) | 2012-08-02 |
| AU2007211319B9 (en) | 2012-05-31 |
| EA200870218A1 (ru) | 2009-02-27 |
| AU2007211319B2 (en) | 2012-01-19 |
| EA019385B1 (ru) | 2014-03-31 |
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