JP2007530690A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2007530690A5 JP2007530690A5 JP2007506284A JP2007506284A JP2007530690A5 JP 2007530690 A5 JP2007530690 A5 JP 2007530690A5 JP 2007506284 A JP2007506284 A JP 2007506284A JP 2007506284 A JP2007506284 A JP 2007506284A JP 2007530690 A5 JP2007530690 A5 JP 2007530690A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- triazole
- trifluoromethyl
- alkyl
- 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.)
- Withdrawn
Links
- -1 hydroxy, amino, carboxy Chemical group 0.000 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 125000001424 substituent group Chemical group 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 6
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000001041 indolyl group Chemical group 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- NTNLPJLHGXIPQN-UHFFFAOYSA-N 1-methyl-4-[4-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazol-3-yl]indole Chemical compound N=1N=C(C=2C=3C=CN(C)C=3C=CC=2)N(C)C=1C1=CC=CC=C1C(F)(F)F NTNLPJLHGXIPQN-UHFFFAOYSA-N 0.000 claims 1
- 102100036506 11-beta-hydroxysteroid dehydrogenase 1 Human genes 0.000 claims 1
- 101710186107 11-beta-hydroxysteroid dehydrogenase 1 Proteins 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- HNZNQYMAJIIXRK-UHFFFAOYSA-N 3,5-bis(2,3-dichlorophenyl)-4-methyl-1,2,4-triazole Chemical compound CN1C(C=2C(=C(Cl)C=CC=2)Cl)=NN=C1C1=CC=CC(Cl)=C1Cl HNZNQYMAJIIXRK-UHFFFAOYSA-N 0.000 claims 1
- YSTNAQKFFUCUFF-UHFFFAOYSA-N 3,5-bis(2,4-dimethylphenyl)-4-methyl-1,2,4-triazole Chemical compound CC1=CC(C)=CC=C1C(N1C)=NN=C1C1=CC=C(C)C=C1C YSTNAQKFFUCUFF-UHFFFAOYSA-N 0.000 claims 1
- SKWYKJHAARIWNY-UHFFFAOYSA-N 3,5-bis(2-chlorophenyl)-4-methyl-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)Cl)=NN=C1C1=CC=CC=C1Cl SKWYKJHAARIWNY-UHFFFAOYSA-N 0.000 claims 1
- JHFZCCZCHICRJQ-UHFFFAOYSA-N 3-(1-methoxynaphthalen-2-yl)-4-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound C1=CC2=CC=CC=C2C(OC)=C1C(N1C)=NN=C1C1=CC=CC=C1C(F)(F)F JHFZCCZCHICRJQ-UHFFFAOYSA-N 0.000 claims 1
- SOPZURRJHOEIOK-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)-4-methyl-5-(2-methylphenyl)-1,2,4-triazole Chemical compound CC1=CC=CC=C1C(N1C)=NN=C1C1=CC=CC(Cl)=C1Cl SOPZURRJHOEIOK-UHFFFAOYSA-N 0.000 claims 1
- YZFAQSSIHAAJRY-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)-5-(2-methoxyphenyl)-4-methyl-1,2,4-triazole Chemical compound COC1=CC=CC=C1C(N1C)=NN=C1C1=CC=CC(Cl)=C1Cl YZFAQSSIHAAJRY-UHFFFAOYSA-N 0.000 claims 1
- OOZPYYLPXHCVTL-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-5-(2-ethylsulfanylphenyl)-4-methyl-1,2,4-triazole Chemical compound CCSC1=CC=CC=C1C(N1C)=NN=C1C1=CC=C(Cl)C=C1Cl OOZPYYLPXHCVTL-UHFFFAOYSA-N 0.000 claims 1
- CYPQHTJOGCYFOC-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-4-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)C(F)(F)F)=NN=C1C1=C(Cl)C=CC=C1Cl CYPQHTJOGCYFOC-UHFFFAOYSA-N 0.000 claims 1
- LZSNOGCKVOHLDL-UHFFFAOYSA-N 3-(2-bromophenyl)-4-methyl-5-(2-methylphenyl)-1,2,4-triazole Chemical compound CC1=CC=CC=C1C(N1C)=NN=C1C1=CC=CC=C1Br LZSNOGCKVOHLDL-UHFFFAOYSA-N 0.000 claims 1
- MBOZUGMFGFMJRX-UHFFFAOYSA-N 3-(2-bromophenyl)-4-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)Br)=NN=C1C1=CC=CC=C1C(F)(F)F MBOZUGMFGFMJRX-UHFFFAOYSA-N 0.000 claims 1
- DJHDWMXPENBKGA-UHFFFAOYSA-N 3-(2-bromophenyl)-5-(2-chlorophenyl)-4-methyl-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)Cl)=NN=C1C1=CC=CC=C1Br DJHDWMXPENBKGA-UHFFFAOYSA-N 0.000 claims 1
- QMPIIRBLTUIZOA-UHFFFAOYSA-N 3-(2-bromophenyl)-5-(2-methoxyphenyl)-4-methyl-1,2,4-triazole Chemical compound COC1=CC=CC=C1C(N1C)=NN=C1C1=CC=CC=C1Br QMPIIRBLTUIZOA-UHFFFAOYSA-N 0.000 claims 1
- RISKLUFTIJVKSQ-UHFFFAOYSA-N 3-(2-chloro-4-ethylsulfanylphenyl)-5-(2-fluorophenyl)-4-methyl-1,2,4-triazole Chemical compound ClC1=CC(SCC)=CC=C1C(N1C)=NN=C1C1=CC=CC=C1F RISKLUFTIJVKSQ-UHFFFAOYSA-N 0.000 claims 1
- IYJZNIQXCCQOQI-UHFFFAOYSA-N 3-(2-chloro-4-fluorophenyl)-5-(2-chlorophenyl)-4-methyl-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)Cl)=NN=C1C1=CC=C(F)C=C1Cl IYJZNIQXCCQOQI-UHFFFAOYSA-N 0.000 claims 1
- QNMPWTBJPOAEDR-UHFFFAOYSA-N 3-(2-chlorophenyl)-4-methyl-5-[2-(trifluoromethoxy)phenyl]-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)Cl)=NN=C1C1=CC=CC=C1OC(F)(F)F QNMPWTBJPOAEDR-UHFFFAOYSA-N 0.000 claims 1
- AGZNKNKKQJFMDU-UHFFFAOYSA-N 3-(2-chlorophenyl)-4-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)Cl)=NN=C1C1=CC=CC=C1C(F)(F)F AGZNKNKKQJFMDU-UHFFFAOYSA-N 0.000 claims 1
- QEVDPEQVRDLTHF-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-(2,3-dichlorophenyl)-4-methyl-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)Cl)=NN=C1C1=CC=CC(Cl)=C1Cl QEVDPEQVRDLTHF-UHFFFAOYSA-N 0.000 claims 1
- ZCFPMOQXMQWXEP-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-[2-chloro-3-(trifluoromethyl)phenyl]-4-methyl-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)Cl)=NN=C1C1=CC=CC(C(F)(F)F)=C1Cl ZCFPMOQXMQWXEP-UHFFFAOYSA-N 0.000 claims 1
- VNNVZCOWLMLJSK-UHFFFAOYSA-N 3-(2-cyclopropylphenyl)-5-(2,4-dichlorophenyl)-4-methyl-1,2,4-triazole Chemical compound CN1C(C=2C(=CC(Cl)=CC=2)Cl)=NN=C1C1=CC=CC=C1C1CC1 VNNVZCOWLMLJSK-UHFFFAOYSA-N 0.000 claims 1
- HEXZJRBEVHEMHA-UHFFFAOYSA-N 3-(2-ethoxyphenyl)-4-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CCOC1=CC=CC=C1C(N1C)=NN=C1C1=CC=CC=C1C(F)(F)F HEXZJRBEVHEMHA-UHFFFAOYSA-N 0.000 claims 1
- CHPFOFYMIRFOLW-UHFFFAOYSA-N 3-(2-methoxyphenyl)-4-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound COC1=CC=CC=C1C(N1C)=NN=C1C1=CC=CC=C1C(F)(F)F CHPFOFYMIRFOLW-UHFFFAOYSA-N 0.000 claims 1
- POYZNCSBPDZNDU-UHFFFAOYSA-N 3-(3-chloronaphthalen-2-yl)-4-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC3=CC=CC=C3C=2)Cl)N(C)C=1C1=CC=CC=C1C(F)(F)F POYZNCSBPDZNDU-UHFFFAOYSA-N 0.000 claims 1
- FWDPOAPCQUFKJP-UHFFFAOYSA-N 3-(5-chloro-6-methoxynaphthalen-1-yl)-4-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound C=1C=CC2=C(Cl)C(OC)=CC=C2C=1C(N1C)=NN=C1C1=CC=CC=C1C(F)(F)F FWDPOAPCQUFKJP-UHFFFAOYSA-N 0.000 claims 1
- UHUOSJYWUHGRMS-UHFFFAOYSA-N 3-[2-(4-chlorophenoxy)phenyl]-4-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)OC=2C=CC(Cl)=CC=2)=NN=C1C1=CC=CC=C1C(F)(F)F UHUOSJYWUHGRMS-UHFFFAOYSA-N 0.000 claims 1
- UUXYDXHRHCAPFP-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)sulfanylphenyl]-4-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)SC=2C=CC(Cl)=CC=2)=NN=C1C1=CC=CC=C1C(F)(F)F UUXYDXHRHCAPFP-UHFFFAOYSA-N 0.000 claims 1
- FTXYRYYOOWJDNF-UHFFFAOYSA-N 3-[2-(4-fluorophenoxy)phenyl]-4-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)OC=2C=CC(F)=CC=2)=NN=C1C1=CC=CC=C1C(F)(F)F FTXYRYYOOWJDNF-UHFFFAOYSA-N 0.000 claims 1
- TYFFATWJXTWJOA-UHFFFAOYSA-N 3-[2-(difluoromethoxy)phenyl]-4-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)OC(F)F)=NN=C1C1=CC=CC=C1C(F)(F)F TYFFATWJXTWJOA-UHFFFAOYSA-N 0.000 claims 1
- YTHVYFZAJHQZDM-UHFFFAOYSA-N 3-[4-(4-chlorophenoxy)phenyl]-4-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1C(C=2C=CC(OC=3C=CC(Cl)=CC=3)=CC=2)=NN=C1C1=CC=CC=C1C(F)(F)F YTHVYFZAJHQZDM-UHFFFAOYSA-N 0.000 claims 1
- NZGFCTSUVFOUQD-UHFFFAOYSA-N 3-[4-chloro-5-(2-chlorophenyl)-1-methylpyrazol-3-yl]-4-methyl-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1N=C(C=2N(C(C=3C(=CC=CC=3)C(F)(F)F)=NN=2)C)C(Cl)=C1C1=CC=CC=C1Cl NZGFCTSUVFOUQD-UHFFFAOYSA-N 0.000 claims 1
- PFUFMNONWYFELD-UHFFFAOYSA-N 4-[4-methyl-5-(1,2,3-trimethylindol-5-yl)-1,2,4-triazol-3-yl]phenol Chemical compound C=1C=C2N(C)C(C)=C(C)C2=CC=1C(N1C)=NN=C1C1=CC=C(O)C=C1 PFUFMNONWYFELD-UHFFFAOYSA-N 0.000 claims 1
- IGNNXZFHMSPANF-UHFFFAOYSA-N 4-[5-(2-chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]-1-methylindole Chemical compound N=1N=C(C=2C=3C=CN(C)C=3C=CC=2)N(C)C=1C1=CC=CC=C1Cl IGNNXZFHMSPANF-UHFFFAOYSA-N 0.000 claims 1
- CKRIFUKNNIFAOQ-UHFFFAOYSA-N 4-methyl-3,5-bis[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)C(F)(F)F)=NN=C1C1=CC=CC=C1C(F)(F)F CKRIFUKNNIFAOQ-UHFFFAOYSA-N 0.000 claims 1
- KDVCRAPVYUBSJJ-UHFFFAOYSA-N 4-methyl-3-(2,4,6-trichloronaphthalen-1-yl)-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C3=CC=C(Cl)C=C3C(Cl)=CC=2Cl)N(C)C=1C1=CC=CC=C1C(F)(F)F KDVCRAPVYUBSJJ-UHFFFAOYSA-N 0.000 claims 1
- BQCSQMTYTKDYHB-UHFFFAOYSA-N 4-methyl-3-(2-methylphenyl)-5-[2-(trifluoromethoxy)phenyl]-1,2,4-triazole Chemical compound CC1=CC=CC=C1C(N1C)=NN=C1C1=CC=CC=C1OC(F)(F)F BQCSQMTYTKDYHB-UHFFFAOYSA-N 0.000 claims 1
- NHCKUTVPDTXTNB-UHFFFAOYSA-N 4-methyl-3-(2-phenoxyphenyl)-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)=NN=C1C1=CC=CC=C1C(F)(F)F NHCKUTVPDTXTNB-UHFFFAOYSA-N 0.000 claims 1
- VDAQBZPLWXZQHN-UHFFFAOYSA-N 4-methyl-3-(2-prop-2-ynoxyphenyl)-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)OCC#C)=NN=C1C1=CC=CC=C1C(F)(F)F VDAQBZPLWXZQHN-UHFFFAOYSA-N 0.000 claims 1
- QPXIWXDWBDJNOR-UHFFFAOYSA-N 4-methyl-3-(4-pentylphenyl)-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound C1=CC(CCCCC)=CC=C1C(N1C)=NN=C1C1=CC=CC=C1C(F)(F)F QPXIWXDWBDJNOR-UHFFFAOYSA-N 0.000 claims 1
- DPCGGPAAWMXMJP-UHFFFAOYSA-N 4-methyl-3-[2-(trifluoromethoxy)phenyl]-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound CN1C(C=2C(=CC=CC=2)OC(F)(F)F)=NN=C1C1=CC=CC=C1C(F)(F)F DPCGGPAAWMXMJP-UHFFFAOYSA-N 0.000 claims 1
- GQDCUNTZBUHXEO-UHFFFAOYSA-N 4-methyl-3-[4-methylsulfanyl-2-(trifluoromethyl)phenyl]-5-[2-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound FC(F)(F)C1=CC(SC)=CC=C1C(N1C)=NN=C1C1=CC=CC=C1C(F)(F)F GQDCUNTZBUHXEO-UHFFFAOYSA-N 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- WLYPBMBWKYALCG-UHFFFAOYSA-N [2,4-bis(trifluoromethyl)phenyl]boronic acid Chemical group OB(O)C1=CC=C(C(F)(F)F)C=C1C(F)(F)F WLYPBMBWKYALCG-UHFFFAOYSA-N 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- OUQNCJWPBUSXPR-UHFFFAOYSA-N chembl257963 Chemical compound N=1N=C(C=2C=3C=CN(C)C=3C=CC=2)N(C)C=1C1=CC=C(O)C=C1 OUQNCJWPBUSXPR-UHFFFAOYSA-N 0.000 claims 1
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55734404P | 2004-03-29 | 2004-03-29 | |
| PCT/US2005/009996 WO2005097759A1 (en) | 2004-03-29 | 2005-03-25 | Diaryltriazoles as inhibitors of 11-beta-hydroxysteroid dehydrogenase-1 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007530690A JP2007530690A (ja) | 2007-11-01 |
| JP2007530690A5 true JP2007530690A5 (https=) | 2008-03-21 |
Family
ID=35124988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007506284A Withdrawn JP2007530690A (ja) | 2004-03-29 | 2005-03-25 | １１−β−ヒドロキシステロイドデヒドロゲナーゼ−１の阻害剤としてのジアリールトリアゾール |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US20080255216A1 (https=) |
| EP (1) | EP1732904B1 (https=) |
| JP (1) | JP2007530690A (https=) |
| CN (1) | CN1938286A (https=) |
| AU (1) | AU2005230864A1 (https=) |
| CA (1) | CA2560314A1 (https=) |
| WO (1) | WO2005097759A1 (https=) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1866298A2 (en) | 2005-03-31 | 2007-12-19 | Takeda San Diego, Inc. | Hydroxysteroid dehydrogenase inhibitors |
| BRPI0710479A2 (pt) | 2006-01-18 | 2012-08-14 | Hoffmann La Roche | composto, processo para sua preparaÇço, composiÇço farmacÊutica, uso de um composto e mÉtodo de tratamento de doenÇa ou desosrdem metabàlica. |
| PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
| JP2010500300A (ja) | 2006-08-08 | 2010-01-07 | サノフィ−アベンティス | アリールアミノアリール−アルキル−置換イミダゾリジン−２，４−ジオン、それらの製造法、それらの化合物を含有する薬剤、およびそれらの使用 |
| JP5269795B2 (ja) * | 2006-09-29 | 2013-08-21 | グリーン・クロス・コーポレイション | カンナビノイドｃｂ１受容体アンタゴニストとしてのヘテロアリール−ピラゾール誘導体 |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US8288402B2 (en) * | 2007-12-20 | 2012-10-16 | Bayer Intellectual Property Gmbh | 4-(4-cyano-2-thioaryl)dihydropyrimidinones and their use |
| JP2011507909A (ja) | 2007-12-20 | 2011-03-10 | エンビボ ファーマシューティカルズ インコーポレイテッド | 四置換ベンゼン |
| US20110293520A1 (en) | 2008-06-09 | 2011-12-01 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. | New drug for inhibiting aggregation of proteins involved in diseases linked to protein aggregation and/or neurodegenerative diseases |
| WO2010001946A1 (ja) | 2008-07-03 | 2010-01-07 | アステラス製薬株式会社 | トリアゾール誘導体またはその塩 |
| WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| MX2012001729A (es) | 2009-08-26 | 2012-06-13 | Sanofi Sa | Nuevos hidratos cristalinos de fluoroglicosido heteroaromatico, productos farmaceuticos que comprenden estos compuestos, y su empleo. |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2011157827A1 (de) | 2010-06-18 | 2011-12-22 | 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 |
| EP2683705B1 (de) | 2011-03-08 | 2015-04-22 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683701B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| EP2683698B1 (de) | 2011-03-08 | 2017-10-04 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched 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 |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8895547B2 (en) | 2011-03-08 | 2014-11-25 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| 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 |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP3122740B1 (en) * | 2014-03-28 | 2019-09-18 | Syngenta Participations AG | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| EP3805213A3 (en) | 2015-06-18 | 2021-06-09 | Nippon Soda Co., Ltd. | 1-(2-(ethylsulfonyl)-phenyl)-4-(phenyl)-1h-1,2,3-triazole and 4-(2-(ethylsulfonyl)-phenyl)-1-(phenyl)-1h-1,2,3-triazole and related compounds derivatives as pesticides |
| BR112018001414B1 (pt) * | 2015-07-24 | 2022-02-22 | Syngenta Participations Ag | Compostos derivados de 1, 2, 4-triazol do ponto de vista pesticida com substituintes contendo enxofre, composição pesticida, método para controle de pragas e método para aproteção de material de propagação de plantas do ataque por pragas |
| US11136301B2 (en) * | 2015-08-31 | 2021-10-05 | The Regents of the University of California, A California Corporation et al. | Broad spectrum antiviral compounds and uses thereof |
| CN108026074A (zh) * | 2015-09-28 | 2018-05-11 | 先正达参股股份有限公司 | 具有含硫取代基的杀有害生物活性杂环衍生物 |
| EP3235813A1 (en) | 2016-04-19 | 2017-10-25 | Cidqo 2012, S.L. | Aza-tetra-cyclo derivatives |
| KR102919209B1 (ko) | 2018-08-10 | 2026-01-28 | 다이아핀 테라퓨틱스, 엘엘씨 | 트리-펩타이드 그리고 대사, 심장혈관 및 염증성 장애의 치료 |
| CN113329754A (zh) | 2018-11-20 | 2021-08-31 | 麻雀制药股份有限公司 | 用于施用皮质类固醇的方法 |
| EP4525983A4 (en) | 2022-05-16 | 2025-09-03 | Sparrow Pharmaceuticals Inc | METHODS AND COMPOSITIONS FOR TREATING GLUCOCORTICOID EXCESS |
| GB202216323D0 (en) * | 2022-11-02 | 2022-12-14 | Cerevance Ltd | Novel compounds |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1571481A (en) | 1975-11-26 | 1980-07-16 | Fisons Ltd | 1,2,4-triazolium compounds having pesticidal and plant growth regulating properties |
| DE2653447A1 (de) * | 1975-11-26 | 1977-06-08 | Fisons Ltd | Die verwendung von triazoliumverbindungen als schaedlingsbekaempfungsmittel |
| DE3173083D1 (en) * | 1980-03-22 | 1986-01-16 | Fbc Ltd | Pesticidal heterocyclic compounds, processes for preparing them, compositions containing them, and their use |
| FR2692575B1 (fr) | 1992-06-23 | 1995-06-30 | Sanofi Elf | Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| US5292736A (en) | 1993-02-26 | 1994-03-08 | Sterling Winthrop Inc. | Morpholinoalkylindenes as antiglaucoma agents |
| JP3407088B2 (ja) * | 1994-06-27 | 2003-05-19 | イハラケミカル工業株式会社 | トリアゾール誘導体の製造方法およびその中間体 |
| US5532237A (en) | 1995-02-15 | 1996-07-02 | Merck Frosst Canada, Inc. | Indole derivatives with affinity for the cannabinoid receptor |
| FR2741621B1 (fr) | 1995-11-23 | 1998-02-13 | Sanofi Sa | Nouveaux derives de pyrazole, procede pour leur preparation et compositions pharmaceutiques en contenant |
| EP0979228A4 (en) | 1997-03-18 | 2000-05-03 | Smithkline Beecham Corp | CANNABINOID RECEPTOR AGONISTS |
| KR20010021696A (ko) | 1997-07-11 | 2001-03-15 | 미즈노 마사루 | 퀴놀린 화합물 및 그의 의약용도 |
| AU742425B2 (en) | 1998-06-11 | 2002-01-03 | Merck & Co., Inc. | Spiropiperidine derivatives as melanocortin receptor agonists |
| DE19837627A1 (de) | 1998-08-19 | 2000-02-24 | Bayer Ag | Neue Aminosäureester von Arylsulfonamiden und Analoga |
| WO2000074679A1 (en) | 1999-06-04 | 2000-12-14 | Merck & Co., Inc. | Substituted piperidines as melanocortin-4 receptor agonists |
| TWI279402B (en) | 1999-08-20 | 2007-04-21 | Banyu Pharma Co Ltd | Spiro compounds having NPY antagonistic activities and agents containing the same |
| AU4929601A (en) | 2000-03-23 | 2001-10-03 | Merck & Co Inc | Substituted piperidines as melanocortin receptor agonists |
| EP1268000A4 (en) | 2000-03-23 | 2004-12-29 | Merck & Co Inc | SPIROPIPERID DERIVATIVES AS MELANOCORTIN RECEPTOR AGONISTS |
| CN1500080A (zh) | 2001-02-02 | 2004-05-26 | ����ҩƷ��ҵ��ʽ���� | 稠合杂环化合物 |
| IL157253A0 (en) | 2001-02-28 | 2004-02-19 | Merck & Co Inc | Acylated piperidine derivatives as melanocortin-4 receptor agonists |
| SK287592B6 (sk) | 2001-03-22 | 2011-03-04 | Solvay Pharmaceuticals B. V. | 4,5-Dihydro-1H-pyrazolové deriváty, ktoré majú CB1-antagonistickú účinnosť, spôsob ich prípravy a použitie |
| US6573287B2 (en) | 2001-04-12 | 2003-06-03 | Bristo-Myers Squibb Company | 2,1-oxazoline and 1,2-pyrazoline-based inhibitors of dipeptidyl peptidase IV and method |
| FR2824825B1 (fr) | 2001-05-15 | 2005-05-06 | Servier Lab | Nouveaux derives d'alpha-amino-acides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| ES2257555T3 (es) | 2001-06-20 | 2006-08-01 | MERCK & CO., INC. | Inhibidores de dipeptidilpeptidasa para el tratamiento de la diabetes. |
| EP1406872B1 (en) | 2001-06-20 | 2007-12-19 | Merck & Co., Inc. | Dipeptidyl peptidase inhibitors for the treatment of diabetes |
| GB0115517D0 (en) | 2001-06-25 | 2001-08-15 | Ferring Bv | Novel antidiabetic agents |
| DE60221983T2 (de) | 2001-06-27 | 2008-05-15 | Smithkline Beecham Corp. | Fluorpyrrolidine als dipeptidyl-peptidase inhibitoren |
| JP4300108B2 (ja) | 2001-06-27 | 2009-07-22 | スミスクライン ビーチャム コーポレーション | ジペプチジルペプチダーゼ阻害剤としてのピロリジン類 |
| RU2299066C2 (ru) | 2001-06-27 | 2007-05-20 | Пробиодруг Аг | Новые ингибиторы дипептидилпептидазы iv и их применение в качестве противораковых агентов |
| ES2296979T3 (es) | 2001-06-27 | 2008-05-01 | Smithkline Beecham Corporation | Fluoropirrolidinas como inhibidores de dipeptidil peptidasa. |
| WO2003004496A1 (en) | 2001-07-03 | 2003-01-16 | Novo Nordisk A/S | Dpp-iv-inhibiting purine derivatives for the treatment of diabetes |
| UA74912C2 (en) | 2001-07-06 | 2006-02-15 | Merck & Co Inc | Beta-aminotetrahydroimidazo-(1,2-a)-pyrazines and tetratriazolo-(4,3-a)-pyrazines as inhibitors of dipeptylpeptidase for the treatment or prevention of diabetes |
| WO2003007887A2 (en) | 2001-07-20 | 2003-01-30 | Merck & Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
| US6977264B2 (en) | 2001-07-25 | 2005-12-20 | Amgen Inc. | Substituted piperidines and methods of use |
| WO2003065983A2 (en) * | 2002-02-01 | 2003-08-14 | Merck & Co., Inc. | 11-beta-hydroxysteroid dehydrogenase 1 inhibitors useful for the treatment of diabetes, obesity and dyslipidemia |
| AR040241A1 (es) * | 2002-06-10 | 2005-03-23 | Merck & Co Inc | Inhibidores de la 11-beta-hidroxiesteroide deshidrogrenasa 1 para el tratamiento de la diabetes obesidad y dislipidemia |
-
2005
- 2005-03-25 AU AU2005230864A patent/AU2005230864A1/en not_active Abandoned
- 2005-03-25 WO PCT/US2005/009996 patent/WO2005097759A1/en not_active Ceased
- 2005-03-25 JP JP2007506284A patent/JP2007530690A/ja not_active Withdrawn
- 2005-03-25 CN CNA2005800101374A patent/CN1938286A/zh active Pending
- 2005-03-25 CA CA002560314A patent/CA2560314A1/en not_active Abandoned
- 2005-03-25 EP EP05726137.2A patent/EP1732904B1/en not_active Expired - Lifetime
- 2005-03-25 US US10/593,010 patent/US20080255216A1/en not_active Abandoned
-
2010
- 2010-04-14 US US12/759,737 patent/US8178546B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2007530690A5 (https=) | ||
| JP2010533158A5 (https=) | ||
| JP2015533157A5 (https=) | ||
| RU2352568C9 (ru) | [1,2,4]оксадиазолы (варианты), способ их получения, фармацевтическая композиция и способ ингибирования активации метаботропных глютаматных рецепторов-5 | |
| JP2011502958A5 (https=) | ||
| JP2018535999A5 (https=) | ||
| JP2018507184A5 (https=) | ||
| JP2020515575A5 (https=) | ||
| JP2007523208A5 (https=) | ||
| JP2019518036A5 (https=) | ||
| IL258577A (en) | 2,4-dihydroxy-nicotinamides as apj agonists | |
| RU2012116207A (ru) | Производные индола в качестве модуляторов crac | |
| JP2019537603A5 (https=) | ||
| JP2014511869A5 (https=) | ||
| JP2018530591A5 (https=) | ||
| RU2008141509A (ru) | Mglur5 модуляторы 1 | |
| JP2006503081A5 (https=) | ||
| RU2006127575A (ru) | Соединение триазола и их применение в качестве антагонистов метаботропного рецептора глутамата | |
| JP2010504280A5 (https=) | ||
| RU2006133909A (ru) | Производные азабицикло {3. 1. 0}гексана, применимые в качестве модуляторов допаминовых рецепторов d3 | |
| RU2011103789A (ru) | Производное триазола или его соль | |
| SI2513053T1 (en) | Pyrrolidine carboxylic acid derivatives as G-protein-coupled receptor 43 agonists (GPR43), pharmaceutical composition and methods for use in the treatment of metabolic disorders | |
| JP2007523182A5 (https=) | ||
| JP2014514299A5 (https=) | ||
| RU2008140940A (ru) | Производное триазола или его соль |