RU2009118489A - Органические соединения - Google Patents
Органические соединения Download PDFInfo
- Publication number
- RU2009118489A RU2009118489A RU2009118489/04A RU2009118489A RU2009118489A RU 2009118489 A RU2009118489 A RU 2009118489A RU 2009118489/04 A RU2009118489/04 A RU 2009118489/04A RU 2009118489 A RU2009118489 A RU 2009118489A RU 2009118489 A RU2009118489 A RU 2009118489A
- Authority
- RU
- Russia
- Prior art keywords
- carboxylic acid
- benzoimidazole
- amide
- dichlorophenyl
- dimethylphenyl
- Prior art date
Links
- 150000002894 organic compounds Chemical class 0.000 title 1
- -1 thiocarbamoyl group Chemical group 0.000 claims abstract 144
- 125000000217 alkyl group Chemical group 0.000 claims abstract 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 42
- 239000001257 hydrogen Substances 0.000 claims abstract 42
- 150000002431 hydrogen Chemical class 0.000 claims abstract 25
- 229910052736 halogen Inorganic materials 0.000 claims abstract 22
- 150000002367 halogens Chemical class 0.000 claims abstract 22
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 15
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 15
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 12
- 125000003118 aryl group Chemical group 0.000 claims abstract 11
- 125000003368 amide group Chemical group 0.000 claims abstract 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 5
- 239000000651 prodrug Substances 0.000 claims abstract 5
- 229940002612 prodrug Drugs 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000003277 amino group Chemical group 0.000 claims abstract 4
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims abstract 4
- 125000000565 sulfonamide group Chemical group 0.000 claims abstract 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- 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 46
- 150000001875 compounds Chemical class 0.000 claims 32
- 125000002252 acyl group Chemical group 0.000 claims 9
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 9
- 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
- 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
- 125000004663 dialkyl amino group Chemical group 0.000 claims 6
- XVNRKPCHMYOPPL-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-1,3-benzoxazole-6-carboxylic acid Chemical compound O1C2=CC(C(=O)O)=CC=C2N=C1C1=C(Cl)C=CC=C1Cl XVNRKPCHMYOPPL-UHFFFAOYSA-N 0.000 claims 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 5
- 125000004104 aryloxy group Chemical group 0.000 claims 5
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 5
- GCMNJUJAKQGROZ-UHFFFAOYSA-N 1,2-Dihydroquinolin-2-imine Chemical compound C1=CC=CC2=NC(N)=CC=C21 GCMNJUJAKQGROZ-UHFFFAOYSA-N 0.000 claims 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000005110 aryl thio group Chemical group 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 125000001589 carboacyl group Chemical group 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 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
- WSWPCNMLEVZGSM-UHFFFAOYSA-N 2-(2-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC=C1CCN WSWPCNMLEVZGSM-UHFFFAOYSA-N 0.000 claims 2
- AUCVZEYHEFAWHO-UHFFFAOYSA-N 2-(3-fluorophenyl)ethanamine Chemical compound NCCC1=CC=CC(F)=C1 AUCVZEYHEFAWHO-UHFFFAOYSA-N 0.000 claims 2
- CKLFJWXRWIQYOC-UHFFFAOYSA-N 2-(4-fluorophenyl)ethanamine Chemical compound NCCC1=CC=C(F)C=C1 CKLFJWXRWIQYOC-UHFFFAOYSA-N 0.000 claims 2
- GPWQHYMVUZYWIK-UHFFFAOYSA-N 2-methyl-1,3-benzothiazol-5-amine Chemical compound NC1=CC=C2SC(C)=NC2=C1 GPWQHYMVUZYWIK-UHFFFAOYSA-N 0.000 claims 2
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical compound CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-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
- 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
- GLNDAGDHSLMOKX-UHFFFAOYSA-N coumarin 120 Chemical compound C1=C(N)C=CC2=C1OC(=O)C=C2C GLNDAGDHSLMOKX-UHFFFAOYSA-N 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims 2
- 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 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 claims 2
- XJEVHMGJSYVQBQ-SECBINFHSA-N (1r)-2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2[C@H](N)CCC2=C1 XJEVHMGJSYVQBQ-SECBINFHSA-N 0.000 claims 1
- AAHCONIDGZPHOL-UHFFFAOYSA-N (2-aminophenyl)-pyrrolidin-1-ylmethanone Chemical compound NC1=CC=CC=C1C(=O)N1CCCC1 AAHCONIDGZPHOL-UHFFFAOYSA-N 0.000 claims 1
- FCNYYGBSHBZVKA-AWNIVKPZSA-N (e)-3-[4-[6-[(4-tert-butylphenyl)carbamoyl]-1h-benzimidazol-2-yl]-3,5-dimethylphenyl]prop-2-enoic acid Chemical compound CC1=CC(\C=C\C(O)=O)=CC(C)=C1C1=NC2=CC=C(C(=O)NC=3C=CC(=CC=3)C(C)(C)C)C=C2N1 FCNYYGBSHBZVKA-AWNIVKPZSA-N 0.000 claims 1
- JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 claims 1
- 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
- DCRKTADMSPCDOA-UHFFFAOYSA-N 1-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]-3-(3,4-dimethylphenyl)urea Chemical compound C1=C(C)C(C)=CC=C1NC(=O)NC1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 DCRKTADMSPCDOA-UHFFFAOYSA-N 0.000 claims 1
- KCYRMURRLLYLPU-UHFFFAOYSA-N 1-methyl-3-phenyl-1H-pyrazol-5-amine Chemical compound C1=C(N)N(C)N=C1C1=CC=CC=C1 KCYRMURRLLYLPU-UHFFFAOYSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- WNCUVUUEJZEATP-UHFFFAOYSA-N 2,5-Dimethoxy-phenethylamine Chemical compound COC1=CC=C(OC)C(CCN)=C1 WNCUVUUEJZEATP-UHFFFAOYSA-N 0.000 claims 1
- SGZUIOXFBOVHHT-UHFFFAOYSA-N 2-(2,3-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(=C(C)C=CC=3)C)C2=C1 SGZUIOXFBOVHHT-UHFFFAOYSA-N 0.000 claims 1
- WSMLFVNVEGYPCR-UHFFFAOYSA-N 2-(2,4,6-trichlorophenyl)-3h-benzimidazole-5-carboxylic acid Chemical compound N1C2=CC(C(=O)O)=CC=C2N=C1C1=C(Cl)C=C(Cl)C=C1Cl WSMLFVNVEGYPCR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- VHJKDOLGYMULOP-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)ethanamine Chemical compound NCCC1=CC=C(Cl)C=C1Cl VHJKDOLGYMULOP-UHFFFAOYSA-N 0.000 claims 1
- VQGZTRKXOUWMAC-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)ethanamine Chemical compound CC1=CC=C(CCN)C(C)=C1 VQGZTRKXOUWMAC-UHFFFAOYSA-N 0.000 claims 1
- RNEFNTMBBIKOFO-UHFFFAOYSA-N 2-(2,5-dimethylphenyl)ethanamine Chemical compound CC1=CC=C(C)C(CCN)=C1 RNEFNTMBBIKOFO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- HATVYEGTDPHBRQ-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-1h-indole-6-carboxylic acid Chemical compound N1C2=CC(C(=O)O)=CC=C2C=C1C1=C(Cl)C=CC=C1Cl HATVYEGTDPHBRQ-UHFFFAOYSA-N 0.000 claims 1
- KYMKYRLZDJEQAY-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-6,7-difluoro-3h-benzimidazole-5-carboxylic acid Chemical compound N=1C=2C(F)=C(F)C(C(=O)O)=CC=2NC=1C1=C(Cl)C=CC=C1Cl KYMKYRLZDJEQAY-UHFFFAOYSA-N 0.000 claims 1
- CPMVFVLPIXLXIP-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n,n-diethyl-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N(CC)CC)=CC=C2N=C1C1=C(Cl)C=CC=C1Cl CPMVFVLPIXLXIP-UHFFFAOYSA-N 0.000 claims 1
- CIYLUHNPJNMZFL-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(1,1-dimethyl-2,3-dihydroinden-5-yl)-3h-benzimidazole-5-carboxamide Chemical compound C=1C=C2C(C)(C)CCC2=CC=1NC(=O)C(C=C1N2)=CC=C1N=C2C1=C(Cl)C=CC=C1Cl CIYLUHNPJNMZFL-UHFFFAOYSA-N 0.000 claims 1
- FRHRKFKANGFTLJ-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(2,6-dimethoxyphenyl)-3h-benzimidazole-5-carboxamide Chemical compound COC1=CC=CC(OC)=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 FRHRKFKANGFTLJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- RWZKHJZAPYCBIZ-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(2-methoxyethyl)-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)NCCOC)=CC=C2N=C1C1=C(Cl)C=CC=C1Cl RWZKHJZAPYCBIZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- YCPHUHYAWZSMIZ-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(2-methyl-1,3-benzothiazol-6-yl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C2SC(C)=NC2=CC=C1NC(=O)C(C=C1N2)=CC=C1N=C2C1=C(Cl)C=CC=C1Cl YCPHUHYAWZSMIZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- NDDOCSGERAAADT-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(2-methylquinolin-6-yl)-3h-benzimidazole-5-carboxamide Chemical compound C1=CC2=NC(C)=CC=C2C=C1NC(=O)C(C=C1N2)=CC=C1N=C2C1=C(Cl)C=CC=C1Cl NDDOCSGERAAADT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- PSBLCOPKOHDPIZ-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(2-pyridin-2-ylethyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC(C(=O)NCCC=3N=CC=CC=3)=CC=C2N1 PSBLCOPKOHDPIZ-UHFFFAOYSA-N 0.000 claims 1
- WAWBSAAXAMNLQD-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(2-pyridin-3-ylethyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC(C(=O)NCCC=3C=NC=CC=3)=CC=C2N1 WAWBSAAXAMNLQD-UHFFFAOYSA-N 0.000 claims 1
- DQFNXOJCOVVFIH-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(3,4-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 DQFNXOJCOVVFIH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- JDCFUBOKRFCCAV-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(3,4-dimethylphenyl)-1-ethoxyindole-6-carboxamide Chemical compound C1=C2N(OCC)C(C=3C(=CC=CC=3Cl)Cl)=CC2=CC=C1C(=O)NC1=CC=C(C)C(C)=C1 JDCFUBOKRFCCAV-UHFFFAOYSA-N 0.000 claims 1
- NXPWWTDZRQIYRA-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(3,4-dimethylphenyl)-1-methylbenzimidazole-5-carboxamide Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=CC=C(N(C)C(=N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 NXPWWTDZRQIYRA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- TVJKZIZLMYXVIT-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-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=3Cl)Cl)C2=C1 TVJKZIZLMYXVIT-UHFFFAOYSA-N 0.000 claims 1
- SOVYNCGIMXWXHG-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(3,4-dimethylphenyl)-3h-benzimidazole-5-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 SOVYNCGIMXWXHG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- BIIDWPUAIGSRGO-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-(3,5-dimethoxyphenyl)-3h-benzimidazole-5-carboxamide Chemical compound COC1=CC(OC)=CC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=C1 BIIDWPUAIGSRGO-UHFFFAOYSA-N 0.000 claims 1
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- SYHCELBZCGVXDQ-UHFFFAOYSA-N ethyl n-[2-(2,3-dichlorophenyl)-3h-benzimidazol-5-yl]carbamate Chemical compound N1C2=CC(NC(=O)OCC)=CC=C2N=C1C1=CC=CC(Cl)=C1Cl SYHCELBZCGVXDQ-UHFFFAOYSA-N 0.000 claims 1
- WYDZNVLSCSGJFZ-UHFFFAOYSA-N ethyl n-[2-(2,4-dichlorophenyl)-3h-benzimidazol-5-yl]carbamate Chemical compound N1C2=CC(NC(=O)OCC)=CC=C2N=C1C1=CC=C(Cl)C=C1Cl WYDZNVLSCSGJFZ-UHFFFAOYSA-N 0.000 claims 1
- AHKMWLGXNMVLDS-UHFFFAOYSA-N ethyl n-[2-(2,6-dimethylphenyl)-3h-benzimidazol-5-yl]carbamate Chemical compound N1C2=CC(NC(=O)OCC)=CC=C2N=C1C1=C(C)C=CC=C1C AHKMWLGXNMVLDS-UHFFFAOYSA-N 0.000 claims 1
- RJHFJGGGPXRMLU-UHFFFAOYSA-N ethyl n-[2-(2-chlorophenyl)-3h-benzimidazol-5-yl]carbamate Chemical compound N1C2=CC(NC(=O)OCC)=CC=C2N=C1C1=CC=CC=C1Cl RJHFJGGGPXRMLU-UHFFFAOYSA-N 0.000 claims 1
- BWCLNKGQMKGHHK-UHFFFAOYSA-N ethyl n-[2-(4-methoxy-2-methylphenyl)-3h-benzimidazol-5-yl]carbamate Chemical compound N1C2=CC(NC(=O)OCC)=CC=C2N=C1C1=CC=C(OC)C=C1C BWCLNKGQMKGHHK-UHFFFAOYSA-N 0.000 claims 1
- FBWNQIIQAMLJMZ-UHFFFAOYSA-N ethyl n-[4-[6-[(3-chlorophenyl)carbamoyl]-1h-benzimidazol-2-yl]-3-methylphenyl]carbamate Chemical compound CC1=CC(NC(=O)OCC)=CC=C1C1=NC2=CC=C(C(=O)NC=3C=C(Cl)C=CC=3)C=C2N1 FBWNQIIQAMLJMZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000004470 heterocyclooxy group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- LEDWGUOLJHIATK-UHFFFAOYSA-N methyl 2-[3,5-dichloro-4-[6-(quinolin-2-ylcarbamoyl)-1h-benzimidazol-2-yl]phenoxy]acetate Chemical compound ClC1=CC(OCC(=O)OC)=CC(Cl)=C1C1=NC2=CC=C(C(=O)NC=3N=C4C=CC=CC4=CC=3)C=C2N1 LEDWGUOLJHIATK-UHFFFAOYSA-N 0.000 claims 1
- YKGMZDTYINCTSB-UHFFFAOYSA-N methyl 2-[3,5-dichloro-4-[6-[(3,4-dimethylphenyl)carbamoyl]-1h-benzimidazol-2-yl]phenoxy]acetate Chemical compound ClC1=CC(OCC(=O)OC)=CC(Cl)=C1C1=NC2=CC=C(C(=O)NC=3C=C(C)C(C)=CC=3)C=C2N1 YKGMZDTYINCTSB-UHFFFAOYSA-N 0.000 claims 1
- BSOOLALKZBPWQL-UHFFFAOYSA-N methyl 2-[3,5-dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1h-benzimidazol-2-yl]phenoxy]acetate Chemical compound CC1=CC(OCC(=O)OC)=CC(C)=C1C1=NC2=CC=C(C(=O)NC=3N=C4C=CC=CC4=CC=3)C=C2N1 BSOOLALKZBPWQL-UHFFFAOYSA-N 0.000 claims 1
- GTOHMBHHBVCSHO-UHFFFAOYSA-N methyl 2-[3-chloro-4-[6-[(3,4-dimethylphenyl)carbamoyl]-1h-benzimidazol-2-yl]phenoxy]acetate Chemical compound ClC1=CC(OCC(=O)OC)=CC=C1C1=NC2=CC=C(C(=O)NC=3C=C(C)C(C)=CC=3)C=C2N1 GTOHMBHHBVCSHO-UHFFFAOYSA-N 0.000 claims 1
- CRYYTXUGXDEEEJ-UHFFFAOYSA-N methyl 2-[4-[6-[(3,4-dimethylphenyl)carbamoyl]-1h-benzimidazol-2-yl]-3,5-dimethylanilino]acetate Chemical compound CC1=CC(NCC(=O)OC)=CC(C)=C1C1=NC2=CC(C(=O)NC=3C=C(C)C(C)=CC=3)=CC=C2N1 CRYYTXUGXDEEEJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- SVGLZEJXLVERSR-UHFFFAOYSA-N methyl 4-[6-[(3-chlorophenyl)carbamoyl]-1h-benzimidazol-2-yl]-3-methylbenzoate Chemical compound CC1=CC(C(=O)OC)=CC=C1C1=NC2=CC=C(C(=O)NC=3C=C(Cl)C=CC=3)C=C2N1 SVGLZEJXLVERSR-UHFFFAOYSA-N 0.000 claims 1
- PJBQKLJBRRYQRE-UHFFFAOYSA-N methyl 4-[6-[(3-chlorophenyl)carbamoyl]-1h-benzimidazol-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC2=CC=C(C(=O)NC=3C=C(Cl)C=CC=3)C=C2N1 PJBQKLJBRRYQRE-UHFFFAOYSA-N 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- LHEBNPASGCMEHK-UHFFFAOYSA-N n,2-bis(3-chlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C=C(Cl)C=CC=2)=C1 LHEBNPASGCMEHK-UHFFFAOYSA-N 0.000 claims 1
- WEZBPUIJKBGVLF-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 WEZBPUIJKBGVLF-UHFFFAOYSA-N 0.000 claims 1
- HBUOANAONKFUNU-UHFFFAOYSA-N n-(2,5-ditert-butylphenyl)-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound CC(C)(C)C1=CC=C(C(C)(C)C)C(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=C1 HBUOANAONKFUNU-UHFFFAOYSA-N 0.000 claims 1
- IZROQFCGAHTMKW-UHFFFAOYSA-N n-(2-adamantyl)-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC=C(C(=O)NC3C4CC5CC(C4)CC3C5)C=C2N1 IZROQFCGAHTMKW-UHFFFAOYSA-N 0.000 claims 1
- LVRBILNLPMFKOJ-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-(4-methoxy-2,6-dimethylphenyl)-3h-benzimidazole-5-carboxamide Chemical compound CC1=CC(OC)=CC(C)=C1C1=NC2=CC=C(C(=O)NC=3C=C(C)C(C)=CC=3)C=C2N1 LVRBILNLPMFKOJ-UHFFFAOYSA-N 0.000 claims 1
- XCFAADYJGUHYPB-UHFFFAOYSA-N n-(3,5-ditert-butylphenyl)-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=C1 XCFAADYJGUHYPB-UHFFFAOYSA-N 0.000 claims 1
- MCTOJJHVRGYANX-UHFFFAOYSA-N n-(3-acetylphenyl)-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound CC(=O)C1=CC=CC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=C1 MCTOJJHVRGYANX-UHFFFAOYSA-N 0.000 claims 1
- PJJZGXCZWRYUAK-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 PJJZGXCZWRYUAK-UHFFFAOYSA-N 0.000 claims 1
- DHSIOCDXOLABRU-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(2,3-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C(=C(Cl)C=CC=2)Cl)=C1 DHSIOCDXOLABRU-UHFFFAOYSA-N 0.000 claims 1
- FEWLSMBORHQWFO-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(2,4-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1 FEWLSMBORHQWFO-UHFFFAOYSA-N 0.000 claims 1
- BUCXXYGSCAUELU-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(2,5-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C(=CC=C(Cl)C=2)Cl)=C1 BUCXXYGSCAUELU-UHFFFAOYSA-N 0.000 claims 1
- UEEDZWRLSGIDOQ-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(2,6-dichlorophenyl)-1h-indole-5-carboxamide Chemical compound ClC1=CC=CC(NC(=O)C=2C=C3C=C(NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=C1 UEEDZWRLSGIDOQ-UHFFFAOYSA-N 0.000 claims 1
- SQMXCWWKJPKRLB-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=C1 SQMXCWWKJPKRLB-UHFFFAOYSA-N 0.000 claims 1
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- ZYJYWOYHWDXHQA-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(2,6-dimethoxyphenyl)-3h-benzimidazole-5-carboxamide Chemical compound COC1=CC=CC(OC)=C1C1=NC2=CC=C(C(=O)NC=3C=C(Cl)C=CC=3)C=C2N1 ZYJYWOYHWDXHQA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WSXCJKDLTQGPDQ-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(2,6-dinitrophenyl)-3h-benzimidazole-5-carboxamide Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1C1=NC2=CC=C(C(=O)NC=3C=C(Cl)C=CC=3)C=C2N1 WSXCJKDLTQGPDQ-UHFFFAOYSA-N 0.000 claims 1
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- LBGFRTRZONYMQD-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(2-fluorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound FC1=CC=CC=C1C1=NC2=CC=C(C(=O)NC=3C=C(Cl)C=CC=3)C=C2N1 LBGFRTRZONYMQD-UHFFFAOYSA-N 0.000 claims 1
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- XUUATQZHKTZJBM-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(2-methoxyphenyl)-3h-benzimidazole-5-carboxamide Chemical compound COC1=CC=CC=C1C1=NC2=CC=C(C(=O)NC=3C=C(Cl)C=CC=3)C=C2N1 XUUATQZHKTZJBM-UHFFFAOYSA-N 0.000 claims 1
- LJFNLUBRQIPOSO-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(2-methylphenyl)-3h-benzimidazole-5-carboxamide Chemical compound CC1=CC=CC=C1C1=NC2=CC=C(C(=O)NC=3C=C(Cl)C=CC=3)C=C2N1 LJFNLUBRQIPOSO-UHFFFAOYSA-N 0.000 claims 1
- IKYZARBCMLTEJM-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(3-phenoxyphenyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C=C(OC=3C=CC=CC=3)C=CC=2)=C1 IKYZARBCMLTEJM-UHFFFAOYSA-N 0.000 claims 1
- ZAVBFNPWXDQRQN-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(4-chlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=NC2=CC=C(C(=O)NC=3C=C(Cl)C=CC=3)C=C2N1 ZAVBFNPWXDQRQN-UHFFFAOYSA-N 0.000 claims 1
- YHUGGNBVYIXLQL-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(4-cyanophenyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C=CC(=CC=2)C#N)=C1 YHUGGNBVYIXLQL-UHFFFAOYSA-N 0.000 claims 1
- CNVSYMCPWVAUNV-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(4-methoxynaphthalen-1-yl)-3h-benzimidazole-5-carboxamide Chemical compound C12=CC=CC=C2C(OC)=CC=C1C(NC1=C2)=NC1=CC=C2C(=O)NC1=CC=CC(Cl)=C1 CNVSYMCPWVAUNV-UHFFFAOYSA-N 0.000 claims 1
- RQCLSUXEYQUODH-UHFFFAOYSA-N n-(3-chlorophenyl)-2-[2-(trifluoromethyl)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1C1=NC2=CC=C(C(=O)NC=3C=C(Cl)C=CC=3)C=C2N1 RQCLSUXEYQUODH-UHFFFAOYSA-N 0.000 claims 1
- WFGATYYLYGRGDD-UHFFFAOYSA-N n-(3-chlorophenyl)-2-naphthalen-1-yl-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C3=CC=CC=C3C=CC=2)=C1 WFGATYYLYGRGDD-UHFFFAOYSA-N 0.000 claims 1
- RQBKTHXMUYPALI-UHFFFAOYSA-N n-(3-chlorophenyl)-2-phenyl-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C=CC=CC=2)=C1 RQBKTHXMUYPALI-UHFFFAOYSA-N 0.000 claims 1
- YMOOYGHIRJKVSI-UHFFFAOYSA-N n-(3-cyanophenyl)-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC=C(C(=O)NC=3C=C(C=CC=3)C#N)C=C2N1 YMOOYGHIRJKVSI-UHFFFAOYSA-N 0.000 claims 1
- AJKSCRLJCBAXNZ-UHFFFAOYSA-N n-(4-butan-2-ylphenyl)-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound C1=CC(C(C)CC)=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 AJKSCRLJCBAXNZ-UHFFFAOYSA-N 0.000 claims 1
- OZIFHPOSPJGWIX-UHFFFAOYSA-N n-(4-butylphenyl)-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound C1=CC(CCCC)=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 OZIFHPOSPJGWIX-UHFFFAOYSA-N 0.000 claims 1
- GLUCVAZWFKCTHF-UHFFFAOYSA-N n-(4-chlorophenyl)-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 GLUCVAZWFKCTHF-UHFFFAOYSA-N 0.000 claims 1
- NFVNRHLVPVKQNN-UHFFFAOYSA-N n-(4-cyclohexylphenyl)-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)C3CCCCC3)C=C2N1 NFVNRHLVPVKQNN-UHFFFAOYSA-N 0.000 claims 1
- XFLDCRQZQAUKJM-UHFFFAOYSA-N n-(4-tert-butylcyclohexyl)-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound C1CC(C(C)(C)C)CCC1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 XFLDCRQZQAUKJM-UHFFFAOYSA-N 0.000 claims 1
- ORIWRQNCHVBCHR-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1NC(=O)C1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 ORIWRQNCHVBCHR-UHFFFAOYSA-N 0.000 claims 1
- VQRIJPGESYELLJ-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-(2,6-dimethylphenyl)-1h-indole-6-carboxamide Chemical compound CC1=CC=CC(C)=C1C1=CC2=CC=C(C(=O)NC=3C=CC(=CC=3)C(C)(C)C)C=C2N1 VQRIJPGESYELLJ-UHFFFAOYSA-N 0.000 claims 1
- HXTVSUMBKIOACJ-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-(2,6-dimethylphenyl)-3h-benzimidazole-5-carboxamide Chemical compound CC1=CC=CC(C)=C1C1=NC2=CC=C(C(=O)NC=3C=CC(=CC=3)C(C)(C)C)C=C2N1 HXTVSUMBKIOACJ-UHFFFAOYSA-N 0.000 claims 1
- BTSYTBGWNWVBOM-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-(2,6-dichlorophenyl)-1,3-benzoxazole-6-carboxamide Chemical compound ClC1=CC=CC=C1CNC(=O)C1=CC=C(N=C(O2)C=3C(=CC=CC=3Cl)Cl)C2=C1 BTSYTBGWNWVBOM-UHFFFAOYSA-N 0.000 claims 1
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- ICPWNAVDMJVVLV-UHFFFAOYSA-N n-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]-2,4,6-trimethylbenzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 ICPWNAVDMJVVLV-UHFFFAOYSA-N 0.000 claims 1
- SHUSJJVYTCSMDL-UHFFFAOYSA-N n-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]-2-ethoxyacetamide Chemical compound N1C2=CC(NC(=O)COCC)=CC=C2N=C1C1=C(Cl)C=CC=C1Cl SHUSJJVYTCSMDL-UHFFFAOYSA-N 0.000 claims 1
- FRBXURRQRBXLLJ-UHFFFAOYSA-N n-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]-2-phenylacetamide Chemical compound ClC1=CC=CC(Cl)=C1C(NC1=C2)=NC1=CC=C2NC(=O)CC1=CC=CC=C1 FRBXURRQRBXLLJ-UHFFFAOYSA-N 0.000 claims 1
- YZMSCWDRTZLCMG-UHFFFAOYSA-N n-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]-3,4-dimethylbenzamide Chemical compound C1=C(C)C(C)=CC=C1C(=O)NC1=CC=C(N=C(N2)C=3C(=CC=CC=3Cl)Cl)C2=C1 YZMSCWDRTZLCMG-UHFFFAOYSA-N 0.000 claims 1
- XEQPLAVJQUSUSV-UHFFFAOYSA-N n-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)NC=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=C1 XEQPLAVJQUSUSV-UHFFFAOYSA-N 0.000 claims 1
- SNDPNPSGGLBSRS-UHFFFAOYSA-N n-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]-3-methylbutanamide Chemical compound N1C2=CC(NC(=O)CC(C)C)=CC=C2N=C1C1=C(Cl)C=CC=C1Cl SNDPNPSGGLBSRS-UHFFFAOYSA-N 0.000 claims 1
- ZYYNHYNFBGFGRG-UHFFFAOYSA-N n-[2-(2,6-dichlorophenyl)-3h-benzimidazol-5-yl]butanamide Chemical compound N1C2=CC(NC(=O)CCC)=CC=C2N=C1C1=C(Cl)C=CC=C1Cl ZYYNHYNFBGFGRG-UHFFFAOYSA-N 0.000 claims 1
- JMUVLNKNYRPLPJ-UHFFFAOYSA-N n-[4-chloro-3-(trifluoromethyl)phenyl]-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)C=2C=C3NC(=NC3=CC=2)C=2C(=CC=CC=2Cl)Cl)=C1 JMUVLNKNYRPLPJ-UHFFFAOYSA-N 0.000 claims 1
- ZDDAWDQRIYSJFF-UHFFFAOYSA-N n-anthracen-2-yl-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC=C(C(=O)NC=3C=C4C=C5C=CC=CC5=CC4=CC=3)C=C2N1 ZDDAWDQRIYSJFF-UHFFFAOYSA-N 0.000 claims 1
- NBYLOJRCMUNYJL-UHFFFAOYSA-N n-benzyl-2-(2,6-dichlorophenyl)-1,3-benzoxazole-6-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC=C(C(=O)NCC=3C=CC=CC=3)C=C2O1 NBYLOJRCMUNYJL-UHFFFAOYSA-N 0.000 claims 1
- FBRNNPOOEKZFCD-UHFFFAOYSA-N n-benzyl-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC=C(C(=O)NCC=3C=CC=CC=3)C=C2N1 FBRNNPOOEKZFCD-UHFFFAOYSA-N 0.000 claims 1
- CYBDSOKHVZDIHU-UHFFFAOYSA-N n-butyl-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)NCCCC)=CC=C2N=C1C1=C(Cl)C=CC=C1Cl CYBDSOKHVZDIHU-UHFFFAOYSA-N 0.000 claims 1
- YPIDHHKJCRIOCR-UHFFFAOYSA-N n-cyclohexyl-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC=C(C(=O)NC3CCCCC3)C=C2N1 YPIDHHKJCRIOCR-UHFFFAOYSA-N 0.000 claims 1
- IBRPQNMZKVXCIC-UHFFFAOYSA-N n-decyl-2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)NCCCCCCCCCC)=CC=C2N=C1C1=C(Cl)C=CC=C1Cl IBRPQNMZKVXCIC-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 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 compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 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
- RZAUIOKDXQWSQE-UHFFFAOYSA-N quinolin-7-amine Chemical compound C1=CC=NC2=CC(N)=CC=C21 RZAUIOKDXQWSQE-UHFFFAOYSA-N 0.000 claims 1
- MSGRFBKVMUKEGZ-UHFFFAOYSA-N quinoxalin-6-amine Chemical compound N1=CC=NC2=CC(N)=CC=C21 MSGRFBKVMUKEGZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- RZQLKBSMBGXSME-UHFFFAOYSA-N tert-butyl 3-[4-[6-[(3,4-dimethylphenyl)carbamoyl]-1h-benzimidazol-2-yl]-3,5-dimethylphenyl]propanoate Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=CC=C(NC(=N2)C=3C(=CC(CCC(=O)OC(C)(C)C)=CC=3C)C)C2=C1 RZQLKBSMBGXSME-UHFFFAOYSA-N 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 0 Cc1c(*)c(*)c(cncc2)c2c1* Chemical compound Cc1c(*)c(*)c(cncc2)c2c1* 0.000 description 4
Classifications
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- C07D417/12—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 chain containing hetero atoms as chain links
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- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- Endocrinology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (4)
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| US82998006P | 2006-10-18 | 2006-10-18 | |
| US60/829,980 | 2006-10-18 | ||
| US95234107P | 2007-07-27 | 2007-07-27 | |
| US60/952,341 | 2007-07-27 |
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| RU2009118489A true RU2009118489A (ru) | 2010-11-27 |
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| RU2009118489/04A RU2009118489A (ru) | 2006-10-18 | 2007-10-17 | Органические соединения |
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| Country | Link |
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| US (1) | US8222248B2 (enExample) |
| EP (1) | EP2074089B1 (enExample) |
| JP (1) | JP5298022B2 (enExample) |
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| AU (1) | AU2007311087B2 (enExample) |
| BR (1) | BRPI0718478A2 (enExample) |
| CA (1) | CA2666880A1 (enExample) |
| CL (1) | CL2007002974A1 (enExample) |
| ES (1) | ES2440253T3 (enExample) |
| MX (1) | MX2009004047A (enExample) |
| PE (1) | PE20080888A1 (enExample) |
| RU (1) | RU2009118489A (enExample) |
| TW (1) | TW200829563A (enExample) |
| WO (1) | WO2008048991A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2804709C2 (ru) * | 2018-09-18 | 2023-10-04 | Тернс, Инк. | Соединения для лечения некоторых лейкозов |
| US12240835B2 (en) | 2018-09-18 | 2025-03-04 | Terns Pharmaceuticals, Inc. | Substituted benzamides as intermediates in the synthesis of inhibitors of tyrosine kinase enzymatic activity |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006064189A1 (en) | 2004-12-14 | 2006-06-22 | Astrazeneca Ab | Oxadiazole derivatives as dgat inhibitors |
| EP1966221A1 (en) | 2005-12-22 | 2008-09-10 | AstraZeneca AB | Pyrimido- [4, 5-]-oxazines for use as dgat inhibitors |
| CN101460470B (zh) | 2006-05-30 | 2011-05-18 | 阿斯利康(瑞典)有限公司 | 作为dgat1抑制剂的1,3,4-二唑衍生物 |
| 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 |
| WO2009112445A1 (en) * | 2008-03-10 | 2009-09-17 | Novartis Ag | Method of increasing cellular phosphatidyl choline by dgat1 inhibition |
| 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" |
| KR101194995B1 (ko) * | 2009-10-14 | 2012-10-29 | 주식회사 이큐스앤자루 | 신규한 2-페닐-벤즈이미다졸 또는 2-페닐-벤즈옥사졸 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 항바이러스용 약학적 조성물 |
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- 2007-10-16 AR ARP070104573A patent/AR063311A1/es not_active Application Discontinuation
- 2007-10-16 PE PE2007001396A patent/PE20080888A1/es not_active Application Discontinuation
- 2007-10-17 BR BRPI0718478-6A2A patent/BRPI0718478A2/pt not_active IP Right Cessation
- 2007-10-17 ES ES07854118.2T patent/ES2440253T3/es active Active
- 2007-10-17 CA CA002666880A patent/CA2666880A1/en not_active Abandoned
- 2007-10-17 EP EP07854118.2A patent/EP2074089B1/en not_active Not-in-force
- 2007-10-17 US US12/446,088 patent/US8222248B2/en not_active Expired - Fee Related
- 2007-10-17 MX MX2009004047A patent/MX2009004047A/es not_active Application Discontinuation
- 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
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2804709C2 (ru) * | 2018-09-18 | 2023-10-04 | Тернс, Инк. | Соединения для лечения некоторых лейкозов |
| US12240835B2 (en) | 2018-09-18 | 2025-03-04 | Terns Pharmaceuticals, Inc. | Substituted benzamides as intermediates in the synthesis of inhibitors of tyrosine kinase enzymatic activity |
| US12454524B2 (en) | 2018-09-18 | 2025-10-28 | Terns Pharmaceuticals, Inc. | (r)-n-(4-(chlorodifluoromethoxy)phenyl)-2-(difluoromethyl)-1-(1-hydroxypropan-2-yl)-7-(pyrimidin-5-yl)-1H-benzo[d]imidazole-5-carboxamide, or a pharmaceutically acceptable salt or tautomer thereof, for treating certain leukemias |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2009004047A (es) | 2009-07-21 |
| 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 |
| ES2440253T3 (es) | 2014-01-28 |
| 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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