JP2011501735A5 - - Google Patents
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- Publication number
- JP2011501735A5 JP2011501735A5 JP2010526300A JP2010526300A JP2011501735A5 JP 2011501735 A5 JP2011501735 A5 JP 2011501735A5 JP 2010526300 A JP2010526300 A JP 2010526300A JP 2010526300 A JP2010526300 A JP 2010526300A JP 2011501735 A5 JP2011501735 A5 JP 2011501735A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- substituted
- oxadiazol
- unsubstituted
- dichloro
- 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.)
- Granted
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- -1 carboxy, carbamoyl Chemical group 0.000 claims 74
- 125000000217 alkyl group Chemical group 0.000 claims 32
- 150000001875 compounds Chemical class 0.000 claims 30
- 229910052739 hydrogen Inorganic materials 0.000 claims 26
- 239000001257 hydrogen Substances 0.000 claims 26
- 125000001072 heteroaryl group Chemical group 0.000 claims 17
- 150000002431 hydrogen Chemical class 0.000 claims 17
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000002252 acyl group Chemical group 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 8
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000005236 alkanoylamino group Chemical group 0.000 claims 7
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 5
- 125000004104 aryloxy group Chemical group 0.000 claims 5
- 229940124530 sulfonamide Drugs 0.000 claims 5
- 150000003456 sulfonamides Chemical class 0.000 claims 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 102100036869 Diacylglycerol O-acyltransferase 1 Human genes 0.000 claims 3
- 101000927974 Homo sapiens Diacylglycerol O-acyltransferase 1 Proteins 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 3
- 125000005110 aryl thio group Chemical group 0.000 claims 3
- 125000001589 carboacyl group Chemical group 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- OXTKAAXEHMOYSB-UHFFFAOYSA-N 2-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]-4,5-diphenyl-1,3-oxazole Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC=C(C=3OC(=C(N=3)C=3C=CC=CC=3)C=3C=CC=CC=3)C=C2N1 OXTKAAXEHMOYSB-UHFFFAOYSA-N 0.000 claims 1
- HNGVSOBRRWEVHO-UHFFFAOYSA-N 2-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]-5-[6-(trifluoromethyl)pyridin-3-yl]-1,3,4-oxadiazole Chemical compound C1=NC(C(F)(F)F)=CC=C1C1=NN=C(C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)O1 HNGVSOBRRWEVHO-UHFFFAOYSA-N 0.000 claims 1
- UBGWQKWLRPICHU-UHFFFAOYSA-N 2-[3,5-dichloro-4-[6-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]-1h-benzimidazol-2-yl]phenoxy]acetic acid Chemical compound ClC1=CC(OCC(=O)O)=CC(Cl)=C1C1=NC2=CC=C(C=3OC(=NN=3)C=3C=CC(Cl)=CC=3)C=C2N1 UBGWQKWLRPICHU-UHFFFAOYSA-N 0.000 claims 1
- SSCBDEUAEZBUIJ-UHFFFAOYSA-N 2-[4-[6-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]-1h-benzimidazol-2-yl]-3,5-dimethylphenoxy]acetic acid Chemical compound CC1=CC(OCC(O)=O)=CC(C)=C1C1=NC2=CC=C(C=3OC(=NN=3)C=3C=CC(Cl)=CC=3)C=C2N1 SSCBDEUAEZBUIJ-UHFFFAOYSA-N 0.000 claims 1
- SXYZIDPFWLLKCA-UHFFFAOYSA-N 3,5-dimethyl-4-[6-[5-[3-(trifluoromethyl)anilino]-1,3,4-oxadiazol-2-yl]-1H-benzimidazol-2-yl]phenol Chemical compound CC1=CC(O)=CC(C)=C1C1=NC2=CC=C(C=3OC(NC=4C=C(C=CC=4)C(F)(F)F)=NN=3)C=C2N1 SXYZIDPFWLLKCA-UHFFFAOYSA-N 0.000 claims 1
- LNVAFTZCCRGKBM-UHFFFAOYSA-N 3,5-dimethyl-4-[6-[5-[4-(trifluoromethyl)anilino]-1,3,4-oxadiazol-2-yl]-1H-benzimidazol-2-yl]phenol Chemical compound CC1=CC(O)=CC(C)=C1C1=NC2=CC=C(C=3OC(NC=4C=CC(=CC=4)C(F)(F)F)=NN=3)C=C2N1 LNVAFTZCCRGKBM-UHFFFAOYSA-N 0.000 claims 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims 1
- IUXLNGKBZRFMQT-UHFFFAOYSA-N 3-[4-[6-(5-cyclohexyl-1,3,4-oxadiazol-2-yl)-1h-benzimidazol-2-yl]-3,5-dimethylphenyl]-2,2-dimethylpropanoic acid Chemical compound CC1=CC(CC(C)(C)C(O)=O)=CC(C)=C1C1=NC2=CC=C(C=3OC(=NN=3)C3CCCCC3)C=C2N1 IUXLNGKBZRFMQT-UHFFFAOYSA-N 0.000 claims 1
- TUBPDBIOKLNJTG-UHFFFAOYSA-N 3-[4-[6-(5-methoxy-1,3,4-oxadiazol-2-yl)-1h-indol-2-yl]-3,5-dimethylphenyl]propanoic acid Chemical compound O1C(OC)=NN=C1C1=CC=C(C=C(N2)C=3C(=CC(CCC(O)=O)=CC=3C)C)C2=C1 TUBPDBIOKLNJTG-UHFFFAOYSA-N 0.000 claims 1
- ZMGNWJVVHPJXOV-UHFFFAOYSA-N 3-[4-[6-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]-1h-indol-2-yl]-3,5-dimethylphenyl]-2,2-dimethylpropanoic acid Chemical compound CC1=CC(CC(C)(C)C(O)=O)=CC(C)=C1C1=CC2=CC=C(C=3OC(=NN=3)C=3C=CC(Cl)=CC=3)C=C2N1 ZMGNWJVVHPJXOV-UHFFFAOYSA-N 0.000 claims 1
- JOYPWBAZXFFWAK-UHFFFAOYSA-N 3-[4-[6-[5-(4-methoxy-2-methylphenyl)-1,3,4-oxadiazol-2-yl]-1h-benzimidazol-2-yl]-3,5-dimethylphenyl]-2,2-dimethylpropanoic acid Chemical compound CC1=CC(OC)=CC=C1C1=NN=C(C=2C=C3NC(=NC3=CC=2)C=2C(=CC(CC(C)(C)C(O)=O)=CC=2C)C)O1 JOYPWBAZXFFWAK-UHFFFAOYSA-N 0.000 claims 1
- DZTVXQZHWYUNLE-UHFFFAOYSA-N 3-[4-[6-[5-(4-methoxyanilino)-1,3,4-oxadiazol-2-yl]-1h-benzimidazol-2-yl]-3,5-dimethylphenyl]propanoic acid Chemical compound C1=CC(OC)=CC=C1NC1=NN=C(C=2C=C3NC(=NC3=CC=2)C=2C(=CC(CCC(O)=O)=CC=2C)C)O1 DZTVXQZHWYUNLE-UHFFFAOYSA-N 0.000 claims 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims 1
- VCAFQDZGTWSJAS-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]-1,3-oxazole Chemical compound C1=CC(Cl)=CC=C1C1=CN=C(C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)O1 VCAFQDZGTWSJAS-UHFFFAOYSA-N 0.000 claims 1
- FPYKBORVKFNMHS-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]-4-methyl-1,3-oxazole Chemical compound CC=1N=C(C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)OC=1C1=CC=C(Cl)C=C1 FPYKBORVKFNMHS-UHFFFAOYSA-N 0.000 claims 1
- 208000002705 Glucose Intolerance Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- BFPLMTPHDFFMTG-UHFFFAOYSA-N [1,3]oxazolo[5,4-b]pyridine Chemical compound C1=CN=C2OC=NC2=C1 BFPLMTPHDFFMTG-UHFFFAOYSA-N 0.000 claims 1
- WFIHKLWVLPBMIQ-UHFFFAOYSA-N [1,3]thiazolo[5,4-b]pyridine Chemical compound C1=CN=C2SC=NC2=C1 WFIHKLWVLPBMIQ-UHFFFAOYSA-N 0.000 claims 1
- 125000005333 aroyloxy group Chemical group 0.000 claims 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims 1
- 150000001556 benzimidazoles Chemical class 0.000 claims 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004470 heterocyclooxy group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000002460 imidazoles Chemical class 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- RTCQRWIAYHAAMH-UHFFFAOYSA-N n-(2-chloropyridin-4-yl)-5-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]-1,3,4-oxadiazol-2-amine Chemical compound C1=NC(Cl)=CC(NC=2OC(=NN=2)C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=C1 RTCQRWIAYHAAMH-UHFFFAOYSA-N 0.000 claims 1
- HGPIAKILLFPJJN-UHFFFAOYSA-N n-(2-tert-butylpyridin-4-yl)-5-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]-1,3,4-oxadiazol-2-amine Chemical compound C1=NC(C(C)(C)C)=CC(NC=2OC(=NN=2)C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=C1 HGPIAKILLFPJJN-UHFFFAOYSA-N 0.000 claims 1
- RYTPRXOADAOEEW-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-5-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]-1,3,4-oxadiazol-2-amine Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC=C(C=3OC(NC4C5CCC(C5)C4)=NN=3)C=C2N1 RYTPRXOADAOEEW-UHFFFAOYSA-N 0.000 claims 1
- NWZRLVDNPHRTNT-UHFFFAOYSA-N n-(5-chloropyridin-2-yl)-5-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]-1,3,4-oxadiazol-2-amine Chemical compound N1=CC(Cl)=CC=C1NC1=NN=C(C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)O1 NWZRLVDNPHRTNT-UHFFFAOYSA-N 0.000 claims 1
- RQIPEQYAIHAQAG-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-5-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]-1,3,4-oxadiazol-2-amine Chemical compound C1=NC(Cl)=CC=C1NC1=NN=C(C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)O1 RQIPEQYAIHAQAG-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims 1
- 201000009104 prediabetes syndrome Diseases 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97606407P | 2007-09-28 | 2007-09-28 | |
| US60/976,064 | 2007-09-28 | ||
| PCT/EP2008/062900 WO2009040410A1 (en) | 2007-09-28 | 2008-09-26 | Oxadiazole- and oxazole-substituted benzimidazole- and indole-derivatives as dgat1 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011501735A JP2011501735A (ja) | 2011-01-13 |
| JP2011501735A5 true JP2011501735A5 (cg-RX-API-DMAC7.html) | 2011-11-10 |
| JP5675359B2 JP5675359B2 (ja) | 2015-02-25 |
Family
ID=39971086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010526300A Expired - Fee Related JP5675359B2 (ja) | 2007-09-28 | 2008-09-26 | Ｄｇａｔ１阻害剤としてのオキサジアゾールおよびオキサゾール置換ベンゾイミダゾールおよびインドール誘導体 |
Country Status (27)
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2588162A1 (en) | 2004-12-14 | 2006-06-22 | Astrazeneca Ab | Oxadiazole derivatives as dgat inhibitors |
| US7749997B2 (en) | 2005-12-22 | 2010-07-06 | Astrazeneca Ab | Pyrimido [4,5-B] -Oxazines for use as DGAT inhibitors |
| AU2007266796B2 (en) | 2006-05-30 | 2011-02-10 | Astrazeneca Ab | Substituted 5-phenylamino-1,3,4-oxadiazol-2-ylcarbonylamino-4-phenoxy-cyclohexane carboxylic acid as inhibitors of acetyl coenzyme A diacylglycerol acyltransferase |
| AR066169A1 (es) * | 2007-09-28 | 2009-07-29 | Novartis Ag | Derivados de benzo-imidazoles, utiles para trastornos asociados con la actividad de dgat |
| WO2009112445A1 (en) * | 2008-03-10 | 2009-09-17 | Novartis Ag | Method of increasing cellular phosphatidyl choline by dgat1 inhibition |
| US8637507B2 (en) | 2009-03-18 | 2014-01-28 | Merck Sharp & Dohme Corp. | Bicyclic compounds as inhibitors of diacylglycerol acyltransferase |
| US8748426B2 (en) | 2009-12-31 | 2014-06-10 | Piramal Enterprises Limited | Inhibitors of diacylglycerol acyl transferase |
| EP2552441B1 (en) * | 2010-03-30 | 2016-05-04 | Novartis AG | Uses of dgat1 inhibitors |
| WO2012044567A2 (en) * | 2010-09-30 | 2012-04-05 | Merck Sharp & Dohme Corp. | Imidazole derivatives |
| WO2012064569A1 (en) * | 2010-11-08 | 2012-05-18 | Merck Sharp & Dohme Corp. | Imidazole derivatives |
| RU2609200C2 (ru) | 2011-07-08 | 2017-01-30 | Новартис Аг | Способ лечения атеросклероза у субъектов с высоким уровнем триглицеридов |
| WO2013074387A1 (en) * | 2011-11-14 | 2013-05-23 | Merck Sharp & Dohme Corp. | Imidazole derivatives |
| WO2013169648A1 (en) | 2012-05-07 | 2013-11-14 | Novartis Ag | Pharmaceutical combinations comprising a dgat1 inhibtor and a triglyceride lowering drug |
| EP2903985A1 (en) | 2012-10-03 | 2015-08-12 | Advinus Therapeutics Limited | Spirocyclic compounds, compositions and medicinal applications thereof |
| HRP20190099T1 (hr) * | 2012-11-23 | 2019-04-19 | Glaxosmithkline Llc | Novi spojevi kao inhibitori diacilglicerin aciltransferaze |
| WO2014081996A1 (en) * | 2012-11-23 | 2014-05-30 | Glaxosmithkline Llc | Novel compounds as diacylglycerol acyltransferase inhibitors |
| US9796729B2 (en) | 2012-11-23 | 2017-10-24 | Glaxosmithkline Llc | Compounds as diacylglycerol acyltransferase inhibitors |
| CN103087045B (zh) * | 2013-01-11 | 2015-08-12 | 上海交通大学 | 一种苯并咪唑类杂环化合物、药物组合物及其用途 |
| CN104672144A (zh) * | 2015-02-13 | 2015-06-03 | 佛山市赛维斯医药科技有限公司 | 一种环丙基酰肼和硝基苯类gpr119激动剂、制备方法及其用途 |
| CN104610152A (zh) * | 2015-02-13 | 2015-05-13 | 佛山市赛维斯医药科技有限公司 | 一类环丙基酰肼类gpr119激动剂、制备方法及其用途 |
| MY205335A (en) | 2018-03-16 | 2024-10-16 | Anji Pharmaceuticals Inc | Compositions and methods for treating severe constipation |
| WO2020110008A1 (en) | 2018-11-27 | 2020-06-04 | Novartis Ag | Cyclic pentamer compounds as proprotein convertase subtilisin/kexin type 9 (pcsk9) inhibitors for the treatment of metabolic disorder |
| UY38485A (es) | 2018-11-27 | 2020-06-30 | Novartis Ag | Compuestos tetrámeros cíclicos como inhibidores de proproteína convertasa subtilisina/kexina tipo 9 (pcsk9), método de tratamiento, uso y su preparación |
| JP7657151B2 (ja) | 2018-11-27 | 2025-04-04 | ノバルティス アーゲー | 代謝性障害の処置のためのプロタンパク質コンバターゼスブチリシン／ケキシン９型（ｐｃｓｋ９）阻害剤としての環状ペプチド |
| WO2023084449A1 (en) | 2021-11-12 | 2023-05-19 | Novartis Ag | Diaminocyclopentylpyridine derivatives for the treatment of a disease or disorder |
| CN117466863A (zh) * | 2022-07-20 | 2024-01-30 | 盛睿泽华医药科技（苏州）有限公司 | 含芳香族取代基的苯并咪唑化合物及其制备方法和用途 |
Family Cites Families (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69635135T2 (de) | 1995-12-28 | 2006-07-06 | Fujisawa Pharmaceutical Co., Ltd. | Benzimidazolderivate |
| WO2002072549A1 (en) | 2001-03-12 | 2002-09-19 | Millennium Pharmaceuticals, Inc. | Functionalized heterocycles as modulators of chemokine receptor function and methods of use therefor |
| CA2451980C (en) | 2001-08-13 | 2012-12-11 | Janssen Pharmaceutica N.V. | 2-amino-4,5-trisubstituted thiazolyl derivatives and their use against autoimmune disorders |
| WO2004047755A2 (en) | 2002-11-22 | 2004-06-10 | Japan Tobacco Inc. | Fused bicyclic nitrogen-containing heterocycles |
| BR0316948A (pt) * | 2002-12-11 | 2005-10-18 | Lilly Co Eli | Composto, formulação farmacêutica, e, uso de um composto |
| JP4560035B2 (ja) | 2003-01-27 | 2010-10-13 | メルク・シャープ・エンド・ドーム・コーポレイション | 置換ピラゾール、このような化合物を含有する組成物及び使用方法 |
| AR044152A1 (es) * | 2003-05-09 | 2005-08-24 | Bayer Corp | Derivados de alquilarilo, metodo de preparacion y uso para el tratamiento de la obesidad |
| JP3878625B2 (ja) | 2003-06-20 | 2007-02-07 | 松下電器産業株式会社 | 振幅調整回路、モータ駆動制御装置、振幅調整方法、及びモータ駆動制御方法 |
| AR045047A1 (es) | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| EP1653969A4 (en) * | 2003-08-07 | 2006-12-20 | Japan Tobacco Inc | PYRROLO 1,2-B PYRIDAZINE DERIVATIVES |
| WO2005035526A1 (en) | 2003-10-09 | 2005-04-21 | Argenta Discovery Ltd. | Bicyclic compounds and their therapeutic use |
| WO2005080371A1 (en) | 2004-02-12 | 2005-09-01 | Merck & Co., Inc. | Amino heterocyclic modulators of chemokine receptor activity |
| JPWO2005108370A1 (ja) * | 2004-04-16 | 2008-03-21 | 味の素株式会社 | ベンゼン化合物 |
| WO2005121132A1 (ja) | 2004-06-11 | 2005-12-22 | Shionogi & Co., Ltd. | 抗ｈｃｖ作用を有する縮合ヘテロ環化合物 |
| EP1764360A4 (en) | 2004-07-02 | 2010-08-11 | Sankyo Co | UREA DERIVATIVE |
| CN101087769A (zh) | 2004-10-15 | 2007-12-12 | 拜尔药品公司 | 用于治疗肥胖的联苯－4－基－羰基氨基酸衍生物的制备及用途 |
| EP1807396B1 (en) | 2004-10-29 | 2013-06-26 | Merck Sharp & Dohme Corp. | 2-aminopyridine compounds useful as beta-secretase inhibitors for the treatment of alzheimer's disease |
| CA2588162A1 (en) | 2004-12-14 | 2006-06-22 | Astrazeneca Ab | Oxadiazole derivatives as dgat inhibitors |
| EP1845081A4 (en) | 2005-02-01 | 2009-03-25 | Takeda Pharmaceutical | amide |
| KR20080000652A (ko) | 2005-04-19 | 2008-01-02 | 바이엘 파마슈티칼스 코포레이션 | 아릴 알킬산 유도체 및 그의 용도 |
| CA2607121A1 (en) | 2005-05-10 | 2006-11-16 | Christophe Michoud | Diacylglycerol acyltransferase inhibitors |
| JP2008543747A (ja) * | 2005-06-11 | 2008-12-04 | アストラゼネカ アクチボラグ | Ｄｇａｔ阻害剤としてのオキサジアゾール誘導体 |
| EP1912634A4 (en) | 2005-07-29 | 2010-06-09 | Bayer Healthcare Llc | PREPARATION AND USE OF BIPHENYL AMINOACIDAL DERIVATIVES TO TREAT OBESITY |
| WO2007022269A2 (en) | 2005-08-15 | 2007-02-22 | Irm Llc | Compounds and compositions as tpo mimetics |
| CA2669736C (en) | 2005-11-03 | 2017-02-21 | Chembridge Research Laboratories, Inc. | Heterocyclic compounds as tyrosine kinase modulators |
| AU2006316560B2 (en) * | 2005-11-28 | 2011-06-16 | Madrigal Pharmaceuticals, Inc. | Inhibitors of diacyglycerol acyltransferase (DGAT) |
| US7749997B2 (en) | 2005-12-22 | 2010-07-06 | Astrazeneca Ab | Pyrimido [4,5-B] -Oxazines for use as DGAT inhibitors |
| WO2007137103A2 (en) | 2006-05-19 | 2007-11-29 | Abbott Laboratories | Inhibitors of diacylglycerol o-acyltransferase type 1 enzyme |
| US20080064717A1 (en) | 2006-05-19 | 2008-03-13 | Rajesh Iyengar | Inhibitors of diacylglycerol O-acyltransferase type 1 enzyme |
| AU2007266796B2 (en) | 2006-05-30 | 2011-02-10 | Astrazeneca Ab | Substituted 5-phenylamino-1,3,4-oxadiazol-2-ylcarbonylamino-4-phenoxy-cyclohexane carboxylic acid as inhibitors of acetyl coenzyme A diacylglycerol acyltransferase |
| NZ572585A (en) | 2006-05-30 | 2011-02-25 | Astrazeneca Ab | 1,3,4-Oxadiazole derivatives as DGAT1 inhibitors |
| CN101460469A (zh) | 2006-06-06 | 2009-06-17 | 阿斯利康(瑞典)有限公司 | 化合物 |
| MX2008015725A (es) | 2006-06-08 | 2009-02-13 | Astrazeneca Ab | Benzimidazolas y su uso para el tratamiento de diabetes. |
| GB0611506D0 (en) | 2006-06-10 | 2006-07-19 | Astrazeneca Ab | Chemical compounds |
| GB0611507D0 (en) | 2006-06-10 | 2006-07-19 | Astrazeneca Ab | Chemical compounds |
| GB0611552D0 (en) | 2006-06-12 | 2006-07-19 | Astrazeneca Ab | Chemical compounds |
| US20120065196A1 (en) | 2006-07-21 | 2012-03-15 | Shuji Kitamura | Amide compounds |
| EP2044055A4 (en) | 2006-07-21 | 2011-03-23 | Takeda Pharmaceutical | amide compounds |
| CA2669884A1 (en) | 2006-11-15 | 2008-05-22 | High Point Pharmaceuticals, Llc | Novel 2-(2-hydroxyphenyl)benzimidazoles useful for treating obesity and diabetes |
| CN101636155A (zh) | 2006-11-29 | 2010-01-27 | 艾博特公司 | 二酰甘油o-酰基转移酶1型酶的抑制剂 |
| WO2008099221A1 (en) | 2007-02-15 | 2008-08-21 | Prosidion Limited | Amide and urea derivatives for the treatment of metabolic diseases |
| GB0707662D0 (en) | 2007-04-20 | 2007-05-30 | Astrazeneca Ab | Chemical compounds |
| JP5383661B2 (ja) | 2007-04-30 | 2014-01-08 | アッヴィ・インコーポレイテッド | ジアシルグリセロールｏ−アシル転移酵素１型酵素の阻害剤 |
| JP2010526781A (ja) | 2007-04-30 | 2010-08-05 | アボット・ラボラトリーズ | ジアシルグリセロールｏ−アシル転移酵素１型酵素の阻害剤 |
| US8115011B2 (en) * | 2007-05-22 | 2012-02-14 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| US8058299B2 (en) * | 2007-05-22 | 2011-11-15 | Via Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| AU2008253118B2 (en) | 2007-05-22 | 2013-11-21 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| US8153644B2 (en) * | 2007-05-22 | 2012-04-10 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| CA2687918C (en) | 2007-06-08 | 2016-11-08 | Janssen Pharmaceutica N.V. | Piperidine/piperazine derivatives |
| CN101678019B (zh) | 2007-06-08 | 2016-03-30 | 詹森药业有限公司 | 哌啶/哌嗪衍生物 |
| AU2008258549B2 (en) | 2007-06-08 | 2013-11-14 | Janssen Pharmaceutica N.V. | Piperidine/piperazine derivatives |
| JO2972B1 (en) | 2007-06-08 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Piperidine / piperazine derivatives |
| WO2009011285A1 (ja) | 2007-07-13 | 2009-01-22 | Taisho Pharmaceutical Co., Ltd. | ヘテロアリールベンゼン化合物 |
| US20090036425A1 (en) | 2007-08-02 | 2009-02-05 | Pfizer Inc | Substituted bicyclolactam compounds |
| US20110092547A1 (en) | 2007-08-17 | 2011-04-21 | Alan Martin Birch | Chemical compounds 979 |
| US20090076275A1 (en) * | 2007-09-19 | 2009-03-19 | David Robert Bolin | Diacylglycerol acyltransferase inhibitors |
| AR066169A1 (es) | 2007-09-28 | 2009-07-29 | Novartis Ag | Derivados de benzo-imidazoles, utiles para trastornos asociados con la actividad de dgat |
| WO2009071483A1 (en) | 2007-12-07 | 2009-06-11 | Via Pharmaceuticals, Inc. | 1- (indaz0l-5-yl) -ureas as diacylglycerol acyltransferase inhibitors |
| EP2234978B1 (en) | 2007-12-20 | 2015-02-25 | AstraZeneca AB | Carbamoyl compounds as dgat1 inhibitors 190 |
| BRPI0913986A2 (pt) | 2008-03-26 | 2015-10-20 | Daiichi Sankyo Co Ltd | composto, composição farmacêutica, e, uso de um composto |
| UY31863A (es) | 2008-06-05 | 2010-01-05 | Janssen Pharmaceutica Nv | Combinaciones de drogas que comprenden un inhibidor de dgat y un agonista de ppar |
| AR072559A1 (es) | 2008-07-15 | 2010-09-08 | Novartis Ag | Amidas sustituidas, composicion farmaceutica que las comprende y su uso en el tratamiento de enfermedades mediadas por dgat1. |
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