ES2440253T3 - Compuestos orgánicos - Google Patents
Compuestos orgánicos Download PDFInfo
- Publication number
- ES2440253T3 ES2440253T3 ES07854118.2T ES07854118T ES2440253T3 ES 2440253 T3 ES2440253 T3 ES 2440253T3 ES 07854118 T ES07854118 T ES 07854118T ES 2440253 T3 ES2440253 T3 ES 2440253T3
- Authority
- ES
- Spain
- Prior art keywords
- benzoimidazol
- phenyl
- amide
- carboxylic acid
- 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.)
- Active
Links
- 150000002894 organic compounds Chemical class 0.000 title description 2
- -1 cycloalkoxycarbonyl Chemical group 0.000 claims abstract description 272
- 150000001875 compounds Chemical class 0.000 claims abstract description 96
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 60
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 42
- 125000003118 aryl group Chemical group 0.000 claims abstract description 36
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 28
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 25
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 23
- 150000002367 halogens Chemical group 0.000 claims abstract description 23
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 21
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 19
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims abstract description 19
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 19
- 125000002252 acyl group Chemical group 0.000 claims abstract description 17
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 14
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims abstract description 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000005236 alkanoylamino group Chemical group 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 103
- MYXFJJLPJSMHEA-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxylic acid Chemical compound N1C2=CC(C(=O)O)=CC=C2N=C1C1=C(Cl)C=CC=C1Cl MYXFJJLPJSMHEA-UHFFFAOYSA-N 0.000 claims description 59
- COYPLDIXZODDDL-UHFFFAOYSA-N 3h-benzimidazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2N=CNC2=C1 COYPLDIXZODDDL-UHFFFAOYSA-N 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 30
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- GCMNJUJAKQGROZ-UHFFFAOYSA-N 1,2-Dihydroquinolin-2-imine Chemical compound C1=CC=CC2=NC(N)=CC=C21 GCMNJUJAKQGROZ-UHFFFAOYSA-N 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 208000008589 Obesity Diseases 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 235000020824 obesity Nutrition 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 12
- 125000001589 carboacyl group Chemical group 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000004423 acyloxy group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000002619 bicyclic group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- RBWJYHBKWYHRJD-UHFFFAOYSA-N 3-[4-[6-[(3,4-dimethylphenyl)carbamoyl]-1h-benzimidazol-2-yl]-3,5-dimethylphenyl]propanoic acid Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=CC=C(NC(=N2)C=3C(=CC(CCC(O)=O)=CC=3C)C)C2=C1 RBWJYHBKWYHRJD-UHFFFAOYSA-N 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 7
- 125000005333 aroyloxy group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 7
- BMTCKKNGHJATLU-UHFFFAOYSA-N 2-(2,6-dimethylphenyl)-3h-benzimidazole-5-carboxylic acid Chemical compound CC1=CC=CC(C)=C1C1=NC2=CC=C(C(O)=O)C=C2N1 BMTCKKNGHJATLU-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229940124597 therapeutic agent Drugs 0.000 claims description 6
- ANXVPQQKQGMQFQ-UHFFFAOYSA-N 2-(4-cyano-2,6-dimethylphenyl)-n-(3,4-dimethylphenyl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC(=CC=3C)C#N)C)C2=C1 ANXVPQQKQGMQFQ-UHFFFAOYSA-N 0.000 claims description 5
- SNTCIFKVANLNAU-UHFFFAOYSA-N 2-[4-[6-[(3,4-dimethylphenyl)carbamoyl]-1h-benzimidazol-2-yl]-3,5-dimethylphenoxy]acetic acid Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC(OCC(O)=O)=CC=3C)C)C2=C1 SNTCIFKVANLNAU-UHFFFAOYSA-N 0.000 claims description 5
- QHBGUDIRKBQHHR-UHFFFAOYSA-N 2-[4-[6-[(3-chlorophenyl)carbamoyl]-1h-benzimidazol-2-yl]-3,5-dimethylphenoxy]acetic acid Chemical compound CC1=CC(OCC(O)=O)=CC(C)=C1C1=NC2=CC=C(C(=O)NC=3C=C(Cl)C=CC=3)C=C2N1 QHBGUDIRKBQHHR-UHFFFAOYSA-N 0.000 claims description 5
- GPWQHYMVUZYWIK-UHFFFAOYSA-N 2-methyl-1,3-benzothiazol-5-amine Chemical compound NC1=CC=C2SC(C)=NC2=C1 GPWQHYMVUZYWIK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000003435 aroyl group Chemical group 0.000 claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- RTGGLKGABFFCFY-UHFFFAOYSA-N n-(4-cyanophenyl)-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC=C(C(=O)NC=3C=CC(=CC=3)C#N)C=C2N1 RTGGLKGABFFCFY-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- YLUJKFNJCYAOQU-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(3,4-dimethylphenyl)-1h-indole-6-carboxamide Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=CC=C(C=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 YLUJKFNJCYAOQU-UHFFFAOYSA-N 0.000 claims description 4
- VTSHJJOTKYSPCH-UHFFFAOYSA-N 2-[3,5-dichloro-4-[6-[(3,4-dimethylphenyl)carbamoyl]-1h-benzimidazol-2-yl]phenoxy]acetic acid Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC(OCC(O)=O)=CC=3Cl)Cl)C2=C1 VTSHJJOTKYSPCH-UHFFFAOYSA-N 0.000 claims description 4
- QMGIRPKEAZNXHA-UHFFFAOYSA-N 2-[4-[6-[(3,4-dimethylphenyl)carbamoyl]-1h-benzimidazol-2-yl]-3,5-dimethylanilino]acetic acid Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=CC=C(NC(=N2)C=3C(=CC(NCC(O)=O)=CC=3C)C)C2=C1 QMGIRPKEAZNXHA-UHFFFAOYSA-N 0.000 claims description 4
- CTMJRCBOVQSOPF-UHFFFAOYSA-N 3-[3,5-dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1h-indol-2-yl]phenyl]propanoic acid Chemical compound CC1=CC(CCC(O)=O)=CC(C)=C1C1=CC2=CC=C(C(=O)NC=3N=C4C=CC=CC4=CC=3)C=C2N1 CTMJRCBOVQSOPF-UHFFFAOYSA-N 0.000 claims description 4
- ADVAEQHHHGGLCE-UHFFFAOYSA-N 4-[6-[(3,4-dimethylphenyl)carbamoyl]-1h-benzimidazol-2-yl]-3,5-dimethylbenzoic acid Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC(=CC=3C)C(O)=O)C)C2=C1 ADVAEQHHHGGLCE-UHFFFAOYSA-N 0.000 claims description 4
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 206010022489 Insulin Resistance Diseases 0.000 claims description 4
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000003524 antilipemic agent Substances 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- YRAZRSHMNFYCCM-UHFFFAOYSA-N ethyl 2-[4-[6-[(3-chlorophenyl)carbamoyl]-1h-benzimidazol-2-yl]-3,5-dimethylphenoxy]acetate Chemical compound CC1=CC(OCC(=O)OCC)=CC(C)=C1C1=NC2=CC=C(C(=O)NC=3C=C(Cl)C=CC=3)C=C2N1 YRAZRSHMNFYCCM-UHFFFAOYSA-N 0.000 claims description 4
- DCKOXQYIDQVQJK-UHFFFAOYSA-N methyl 3-[3,5-dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1h-indol-2-yl]phenyl]propanoate Chemical compound CC1=CC(CCC(=O)OC)=CC(C)=C1C1=CC2=CC=C(C(=O)NC=3N=C4C=CC=CC4=CC=3)C=C2N1 DCKOXQYIDQVQJK-UHFFFAOYSA-N 0.000 claims description 4
- WUFOUVDVYWYQNL-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(2,6-dimethylphenyl)-3h-benzimidazole-5-carboxamide Chemical compound CC1=CC=CC(C)=C1C1=NC2=CC=C(C(=O)NC=3C=C(Cl)C=CC=3)C=C2N1 WUFOUVDVYWYQNL-UHFFFAOYSA-N 0.000 claims description 4
- UZTPLJTWMXRZLQ-UHFFFAOYSA-N n-[2-(3-chlorophenyl)ethyl]-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(CCNC(=O)C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=C1 UZTPLJTWMXRZLQ-UHFFFAOYSA-N 0.000 claims description 4
- CJBKBFMEXJIAOL-UHFFFAOYSA-N n-[[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]methyl]-3,4-dimethylaniline Chemical compound C1=C(C)C(C)=CC=C1NCC1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 CJBKBFMEXJIAOL-UHFFFAOYSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- VNJZZUNFSZZFOJ-UHFFFAOYSA-N 2-(2,4-dichloro-6-methoxyphenyl)-n-quinolin-2-yl-3h-benzimidazole-5-carboxamide Chemical compound COC1=CC(Cl)=CC(Cl)=C1C1=NC2=CC=C(C(=O)NC=3N=C4C=CC=CC4=CC=3)C=C2N1 VNJZZUNFSZZFOJ-UHFFFAOYSA-N 0.000 claims description 3
- SNZCCQSJBHLZGS-UHFFFAOYSA-N 2-(2,6-dichloro-4-hydroxyphenyl)-n-quinolin-2-yl-1h-indole-6-carboxamide Chemical compound ClC1=CC(O)=CC(Cl)=C1C1=CC2=CC=C(C(=O)NC=3N=C4C=CC=CC4=CC=3)C=C2N1 SNZCCQSJBHLZGS-UHFFFAOYSA-N 0.000 claims description 3
- DYGVWBTVMOTNGX-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(2,3-dihydro-1,4-benzodioxin-6-yl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC=C(C(=O)NC=3C=C4OCCOC4=CC=3)C=C2N1 DYGVWBTVMOTNGX-UHFFFAOYSA-N 0.000 claims description 3
- BSJITZHGMYBAHY-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(2-fluorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound FC1=CC=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 BSJITZHGMYBAHY-UHFFFAOYSA-N 0.000 claims description 3
- YBWCRZPMMJQCSX-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(2-methoxyphenyl)-3h-benzimidazole-5-carboxamide Chemical compound COC1=CC=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 YBWCRZPMMJQCSX-UHFFFAOYSA-N 0.000 claims description 3
- ZRIVOIFVOXXVCK-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(2-methyl-1,3-benzothiazol-5-yl)-1,3-benzoxazole-5-carboxamide Chemical compound C=1C=C2SC(C)=NC2=CC=1NC(=O)C(C=C1N=2)=CC=C1OC=2C1=C(Cl)C=CC=C1Cl ZRIVOIFVOXXVCK-UHFFFAOYSA-N 0.000 claims description 3
- AQIOCQCRYYCXHS-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(2-methylphenyl)-3h-benzimidazole-5-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 AQIOCQCRYYCXHS-UHFFFAOYSA-N 0.000 claims description 3
- CZMDDSFSGUJXHX-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(2-phenylethyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC=C(C(=O)NCCC=3C=CC=CC=3)C=C2N1 CZMDDSFSGUJXHX-UHFFFAOYSA-N 0.000 claims description 3
- BINPINNFESAAKN-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(3,4-difluorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C(F)C(F)=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 BINPINNFESAAKN-UHFFFAOYSA-N 0.000 claims description 3
- VLPNJKOZBQPDQV-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(3,4-dimethoxyphenyl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 VLPNJKOZBQPDQV-UHFFFAOYSA-N 0.000 claims description 3
- IBFLZNWXLHFBRI-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(3,4-dimethylphenyl)-1,3-benzoxazole-5-carboxamide Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=CC=C(OC(=N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 IBFLZNWXLHFBRI-UHFFFAOYSA-N 0.000 claims description 3
- CGSJRIINNIPAOB-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(3,5-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC(Cl)=CC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=C1 CGSJRIINNIPAOB-UHFFFAOYSA-N 0.000 claims description 3
- HZSFWRCGKBPPSD-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(3,5-difluorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound FC1=CC(F)=CC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=C1 HZSFWRCGKBPPSD-UHFFFAOYSA-N 0.000 claims description 3
- IAHZFHKSRFYBIJ-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(3-propan-2-yloxyphenyl)-3h-benzimidazole-5-carboxamide Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=C1 IAHZFHKSRFYBIJ-UHFFFAOYSA-N 0.000 claims description 3
- FGWWJFYGKLBTFH-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(4-methoxynaphthalen-2-yl)-3h-benzimidazole-5-carboxamide Chemical compound C=1C2=CC=CC=C2C(OC)=CC=1NC(=O)C(C=C1N2)=CC=C1N=C2C1=C(Cl)C=CC=C1Cl FGWWJFYGKLBTFH-UHFFFAOYSA-N 0.000 claims description 3
- WKJLYZYGOHDCHZ-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(4-methyl-1,3-thiazol-2-yl)-3h-benzimidazole-5-carboxamide Chemical compound CC1=CSC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=N1 WKJLYZYGOHDCHZ-UHFFFAOYSA-N 0.000 claims description 3
- JHYIMZGPDRBFNQ-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(4-methyl-2-oxochromen-7-yl)-3h-benzimidazole-5-carboxamide Chemical compound C1=CC=2C(C)=CC(=O)OC=2C=C1NC(=O)C(C=C1N2)=CC=C1N=C2C1=C(Cl)C=CC=C1Cl JHYIMZGPDRBFNQ-UHFFFAOYSA-N 0.000 claims description 3
- GNAKUNMNOAHRPE-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(4-methylphenyl)-3h-benzimidazole-5-carboxamide Chemical compound C1=CC(C)=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 GNAKUNMNOAHRPE-UHFFFAOYSA-N 0.000 claims description 3
- IGIVGSRTZMQLTR-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(4-methylpyridin-2-yl)-3h-benzimidazole-5-carboxamide Chemical compound CC1=CC=NC(NC(=O)C=2C=C3N=C(NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=C1 IGIVGSRTZMQLTR-UHFFFAOYSA-N 0.000 claims description 3
- URMBQBITVYPSLU-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(4-methylpyrimidin-2-yl)-3h-benzimidazole-5-carboxamide Chemical compound CC1=CC=NC(NC(=O)C=2C=C3N=C(NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=N1 URMBQBITVYPSLU-UHFFFAOYSA-N 0.000 claims description 3
- RRFYULSXAVYNMB-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(4-propan-2-ylphenyl)-3h-benzimidazole-5-carboxamide Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 RRFYULSXAVYNMB-UHFFFAOYSA-N 0.000 claims description 3
- WRIFBJDGTDRCGV-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(5,6,7,8-tetrahydronaphthalen-2-yl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC=C(C(=O)NC=3C=C4CCCCC4=CC=3)C=C2N1 WRIFBJDGTDRCGV-UHFFFAOYSA-N 0.000 claims description 3
- AQLQXEKFBYMCRX-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(5-methylpyridin-2-yl)-3h-benzimidazole-5-carboxamide Chemical compound N1=CC(C)=CC=C1NC(=O)C1=CC=C(NC(=N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 AQLQXEKFBYMCRX-UHFFFAOYSA-N 0.000 claims description 3
- GSOGIHYQFYGAHT-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(5-oxo-7,8-dihydro-6h-naphthalen-2-yl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC=C(C(=O)NC=3C=C4CCCC(=O)C4=CC=3)C=C2N1 GSOGIHYQFYGAHT-UHFFFAOYSA-N 0.000 claims description 3
- UETFFYDUOMPZTD-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(6-methylpyridin-2-yl)-3h-benzimidazole-5-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C=C3N=C(NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=N1 UETFFYDUOMPZTD-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
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Classifications
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| ATE492541T1 (de) | 2006-05-30 | 2011-01-15 | Astrazeneca Ab | Substituierte 5-phenylamino-1,3,4-oxadiazol-2- ylcarbonylamino-4-phenoxycyclohexancarbonsäuren als inhibitoren von acetylcoenzym-a- diacylglycerolacyltransferase |
| JP5662803B2 (ja) | 2007-12-20 | 2015-02-04 | アストラゼネカ アクチボラグ | Dgat1阻害剤としてのカルバモイル化合物190 |
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| WO2010039668A2 (en) * | 2008-10-01 | 2010-04-08 | The Regents Of The University Of California | Inhibitors of cyclin kinase inhibitor p21 |
| GB0821913D0 (en) | 2008-12-02 | 2009-01-07 | Price & Co | Antibacterial compounds |
| US8637507B2 (en) * | 2009-03-18 | 2014-01-28 | Merck Sharp & Dohme Corp. | Bicyclic compounds as inhibitors of diacylglycerol acyltransferase |
| AU2010261499A1 (en) | 2009-06-19 | 2012-01-12 | Astrazeneca Ab | Pyrazine carboxamides as inhibitors of DGAT1 |
| BR112012001532A2 (pt) * | 2009-07-23 | 2019-09-24 | Univ Vanderbilt | "substituída azolesulfonamides benzoimid e indolesulfonamides substituído como potenciadores mglur4" |
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| EA031967B1 (ru) | 2014-10-14 | 2019-03-29 | Вайтаи Фармасьютиклз, Инк. | ДИГИДРОПИРРОЛОПИРИДИНОВЫЕ ИНГИБИТОРЫ ROR-γ |
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- 2007-10-17 TW TW096138922A patent/TW200829563A/zh unknown
- 2007-10-17 RU RU2009118489/04A patent/RU2009118489A/ru not_active Application Discontinuation
- 2007-10-17 JP JP2009533499A patent/JP5298022B2/ja not_active Expired - Fee Related
- 2007-10-17 WO PCT/US2007/081607 patent/WO2008048991A2/en not_active Ceased
- 2007-10-17 KR KR1020097010003A patent/KR20090071642A/ko not_active Withdrawn
- 2007-10-17 AU AU2007311087A patent/AU2007311087B2/en not_active Ceased
- 2007-10-17 CL CL200702974A patent/CL2007002974A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX2009004047A (es) | 2009-07-21 |
| RU2009118489A (ru) | 2010-11-27 |
| CL2007002974A1 (es) | 2008-05-23 |
| BRPI0718478A2 (pt) | 2013-11-26 |
| US8222248B2 (en) | 2012-07-17 |
| WO2008048991A3 (en) | 2008-07-10 |
| CA2666880A1 (en) | 2008-04-28 |
| AU2007311087B2 (en) | 2012-03-01 |
| KR20090071642A (ko) | 2009-07-01 |
| WO2008048991A2 (en) | 2008-04-24 |
| TW200829563A (en) | 2008-07-16 |
| AU2007311087A1 (en) | 2008-04-24 |
| AR063311A1 (es) | 2009-01-21 |
| JP2010506950A (ja) | 2010-03-04 |
| PE20080888A1 (es) | 2008-08-26 |
| EP2074089A2 (en) | 2009-07-01 |
| US20110046133A1 (en) | 2011-02-24 |
| JP5298022B2 (ja) | 2013-09-25 |
| EP2074089B1 (en) | 2013-09-18 |
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