JP2009516685A5 - - Google Patents
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- Publication number
- JP2009516685A5 JP2009516685A5 JP2008541289A JP2008541289A JP2009516685A5 JP 2009516685 A5 JP2009516685 A5 JP 2009516685A5 JP 2008541289 A JP2008541289 A JP 2008541289A JP 2008541289 A JP2008541289 A JP 2008541289A JP 2009516685 A5 JP2009516685 A5 JP 2009516685A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- nicotinamide
- phenyl
- alkyl
- methyl
- 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 acylamine Chemical group 0.000 claims 90
- 125000000217 alkyl group Chemical group 0.000 claims 45
- 229910052736 halogen Inorganic materials 0.000 claims 37
- 150000002367 halogens Chemical class 0.000 claims 37
- 125000002252 acyl group Chemical group 0.000 claims 33
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 32
- 125000003545 alkoxy group Chemical group 0.000 claims 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 30
- 125000000623 heterocyclic group Chemical group 0.000 claims 28
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 24
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 17
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 16
- 235000005152 nicotinamide Nutrition 0.000 claims 16
- 239000011570 nicotinamide Substances 0.000 claims 16
- 229960003966 nicotinamide Drugs 0.000 claims 16
- 125000002837 carbocyclic group Chemical group 0.000 claims 14
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 12
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 12
- 125000001188 haloalkyl group Chemical group 0.000 claims 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 8
- 229940124530 sulfonamide Drugs 0.000 claims 8
- 150000003456 sulfonamides Chemical class 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 241000124008 Mammalia Species 0.000 claims 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 4
- 210000004027 cell Anatomy 0.000 claims 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 229930192474 thiophene Chemical group 0.000 claims 4
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000565 sulfonamide group Chemical group 0.000 claims 3
- 125000004512 1,2,3-thiadiazol-4-yl group Chemical group S1N=NC(=C1)* 0.000 claims 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical group C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 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 2
- CFOBDVARPHSHCM-UHFFFAOYSA-N 6-chloro-n-[4-chloro-3-[(3-chlorobenzoyl)amino]phenyl]-2-methylpyridine-3-carboxamide Chemical compound CC1=NC(Cl)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C=C(Cl)C=CC=2)=C1 CFOBDVARPHSHCM-UHFFFAOYSA-N 0.000 claims 2
- 206010052747 Adenocarcinoma pancreas Diseases 0.000 claims 2
- 206010004146 Basal cell carcinoma Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 2
- 208000000172 Medulloblastoma Diseases 0.000 claims 2
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 2
- 206010041067 Small cell lung cancer Diseases 0.000 claims 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 2
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 201000009036 biliary tract cancer Diseases 0.000 claims 2
- 208000020790 biliary tract neoplasm Diseases 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 201000004101 esophageal cancer Diseases 0.000 claims 2
- 206010017758 gastric cancer Diseases 0.000 claims 2
- 230000009459 hedgehog signaling Effects 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- HHGGELGIWCMDQB-UHFFFAOYSA-N n-[4-chloro-3-[(3-chlorobenzoyl)amino]phenyl]-6-(4-hydroxypiperidin-1-yl)-2-methylpyridine-3-carboxamide Chemical compound CC1=NC(N2CCC(O)CC2)=CC=C1C(=O)NC(C=1)=CC=C(Cl)C=1NC(=O)C1=CC=CC(Cl)=C1 HHGGELGIWCMDQB-UHFFFAOYSA-N 0.000 claims 2
- YZPHNIDWIKXVML-IYBDPMFKSA-N n-[4-chloro-3-[(3-chlorobenzoyl)amino]phenyl]-6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-2-methylpyridine-3-carboxamide Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1C)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C=C(Cl)C=CC=2)=C1 YZPHNIDWIKXVML-IYBDPMFKSA-N 0.000 claims 2
- 201000002094 pancreatic adenocarcinoma Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 2
- 201000011549 stomach cancer Diseases 0.000 claims 2
- FETNLULBCKKKBP-UHFFFAOYSA-N 3-chloro-n-[2-chloro-5-[[4-(1,2,4-triazol-1-yl)benzoyl]amino]phenyl]benzamide Chemical compound ClC1=CC=CC(C(=O)NC=2C(=CC=C(NC(=O)C=3C=CC(=CC=3)N3N=CN=C3)C=2)Cl)=C1 FETNLULBCKKKBP-UHFFFAOYSA-N 0.000 claims 1
- OXUMVKBDTOISIH-UHFFFAOYSA-N 6-(4-acetylpiperazin-1-yl)-n-(3-benzamido-4-chlorophenyl)pyridine-3-carboxamide Chemical compound C1CN(C(=O)C)CCN1C1=CC=C(C(=O)NC=2C=C(NC(=O)C=3C=CC=CC=3)C(Cl)=CC=2)C=N1 OXUMVKBDTOISIH-UHFFFAOYSA-N 0.000 claims 1
- WABQKRNJMBSQMB-UHFFFAOYSA-N 6-(4-acetylpiperazin-1-yl)-n-[4-chloro-3-[(4-chlorobenzoyl)amino]phenyl]pyridine-3-carboxamide Chemical compound C1CN(C(=O)C)CCN1C1=CC=C(C(=O)NC=2C=C(NC(=O)C=3C=CC(Cl)=CC=3)C(Cl)=CC=2)C=N1 WABQKRNJMBSQMB-UHFFFAOYSA-N 0.000 claims 1
- KUFHOIZRNPQYLI-UHFFFAOYSA-N 6-(4-acetylpiperazin-1-yl)-n-[4-chloro-3-[(4-fluorobenzoyl)amino]phenyl]-2-methylpyridine-3-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(N=C1C)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C=CC(F)=CC=2)=C1 KUFHOIZRNPQYLI-UHFFFAOYSA-N 0.000 claims 1
- SJDJALYZTVCQFF-UHFFFAOYSA-N 6-(bromomethyl)-n-[4-chloro-3-[(3-chlorobenzoyl)amino]phenyl]pyridine-3-carboxamide Chemical compound ClC1=CC=CC(C(=O)NC=2C(=CC=C(NC(=O)C=3C=NC(CBr)=CC=3)C=2)Cl)=C1 SJDJALYZTVCQFF-UHFFFAOYSA-N 0.000 claims 1
- SCXOPJLGWZCMOL-UHFFFAOYSA-N 6-[(4-acetylpiperazin-1-yl)methyl]-n-[4-chloro-3-[(3-chlorobenzoyl)amino]phenyl]pyridine-3-carboxamide Chemical compound C1CN(C(=O)C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC(=O)C=3C=C(Cl)C=CC=3)C(Cl)=CC=2)C=N1 SCXOPJLGWZCMOL-UHFFFAOYSA-N 0.000 claims 1
- WRUIXGRWYAORRV-UHFFFAOYSA-N 6-chloro-n-[4-chloro-3-[(2-chlorobenzoyl)amino]phenyl]pyridine-3-carboxamide Chemical compound C1=NC(Cl)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C(=CC=CC=2)Cl)=C1 WRUIXGRWYAORRV-UHFFFAOYSA-N 0.000 claims 1
- KGYYDBVEOJFKON-UHFFFAOYSA-N 6-chloro-n-[4-chloro-3-[(2-fluorobenzoyl)amino]phenyl]pyridine-3-carboxamide Chemical compound FC1=CC=CC=C1C(=O)NC1=CC(NC(=O)C=2C=NC(Cl)=CC=2)=CC=C1Cl KGYYDBVEOJFKON-UHFFFAOYSA-N 0.000 claims 1
- DLAVOYHAYUBYBH-UHFFFAOYSA-N 6-chloro-n-[4-chloro-3-[(3-chlorobenzoyl)amino]phenyl]pyridine-3-carboxamide Chemical compound ClC1=CC=CC(C(=O)NC=2C(=CC=C(NC(=O)C=3C=NC(Cl)=CC=3)C=2)Cl)=C1 DLAVOYHAYUBYBH-UHFFFAOYSA-N 0.000 claims 1
- BKXOMLCZOBVEAG-UHFFFAOYSA-N 6-chloro-n-[4-chloro-3-[(3-fluorobenzoyl)amino]phenyl]pyridine-3-carboxamide Chemical compound FC1=CC=CC(C(=O)NC=2C(=CC=C(NC(=O)C=3C=NC(Cl)=CC=3)C=2)Cl)=C1 BKXOMLCZOBVEAG-UHFFFAOYSA-N 0.000 claims 1
- KGHAIQYAUKVPSR-UHFFFAOYSA-N 6-chloro-n-[4-chloro-3-[(4-chlorobenzoyl)amino]phenyl]pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC1=CC(NC(=O)C=2C=NC(Cl)=CC=2)=CC=C1Cl KGHAIQYAUKVPSR-UHFFFAOYSA-N 0.000 claims 1
- LKXZBHKMXDZFEY-UHFFFAOYSA-N 6-chloro-n-[4-chloro-3-[(4-fluorobenzoyl)amino]phenyl]-2-methylpyridine-3-carboxamide Chemical compound CC1=NC(Cl)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C=CC(F)=CC=2)=C1 LKXZBHKMXDZFEY-UHFFFAOYSA-N 0.000 claims 1
- ZAIGVERZTSUEJI-UHFFFAOYSA-N 6-chloro-n-[4-chloro-3-[(4-fluorobenzoyl)amino]phenyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1=CC(NC(=O)C=2C=NC(Cl)=CC=2)=CC=C1Cl ZAIGVERZTSUEJI-UHFFFAOYSA-N 0.000 claims 1
- 208000005243 Chondrosarcoma Diseases 0.000 claims 1
- 241000289669 Erinaceus europaeus Species 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 201000011066 hemangioma Diseases 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 206010027191 meningioma Diseases 0.000 claims 1
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 1
- OFXDUJXMJLWKKJ-UHFFFAOYSA-N n-(3-amino-4-chlorophenyl)-2-methyl-6-(trifluoromethyl)pyridine-3-carboxamide Chemical compound CC1=NC(C(F)(F)F)=CC=C1C(=O)NC1=CC=C(Cl)C(N)=C1 OFXDUJXMJLWKKJ-UHFFFAOYSA-N 0.000 claims 1
- HDPXTWGIYDZTCD-UHFFFAOYSA-N n-(3-benzamido-4-chlorophenyl)-1-(4-fluorophenyl)-4-methylpyrazole-3-carboxamide Chemical compound CC1=CN(C=2C=CC(F)=CC=2)N=C1C(=O)NC(C=1)=CC=C(Cl)C=1NC(=O)C1=CC=CC=C1 HDPXTWGIYDZTCD-UHFFFAOYSA-N 0.000 claims 1
- BGMXZZNMUQEDLF-UHFFFAOYSA-N n-(3-benzamido-4-chlorophenyl)-2-methyl-4-phenylpyrimidine-5-carboxamide Chemical compound C=1C=CC=CC=1C1=NC(C)=NC=C1C(=O)NC(C=1)=CC=C(Cl)C=1NC(=O)C1=CC=CC=C1 BGMXZZNMUQEDLF-UHFFFAOYSA-N 0.000 claims 1
- INHZYOWKDGYIMC-UHFFFAOYSA-N n-(3-benzamido-4-chlorophenyl)-2-phenyl-1,3-thiazole-4-carboxamide Chemical compound C1=C(NC(=O)C=2C=CC=CC=2)C(Cl)=CC=C1NC(=O)C(N=1)=CSC=1C1=CC=CC=C1 INHZYOWKDGYIMC-UHFFFAOYSA-N 0.000 claims 1
- UTIXROPBIBGHKA-UHFFFAOYSA-N n-(3-benzamido-4-chlorophenyl)-4-methyl-2-phenylpyrimidine-5-carboxamide Chemical compound CC1=NC(C=2C=CC=CC=2)=NC=C1C(=O)NC(C=1)=CC=C(Cl)C=1NC(=O)C1=CC=CC=C1 UTIXROPBIBGHKA-UHFFFAOYSA-N 0.000 claims 1
- DFEYDQWPGMZDLB-UHFFFAOYSA-N n-(3-benzamido-4-chlorophenyl)-6-(3-methylpiperazin-1-yl)pyridine-3-carboxamide Chemical compound C1CNC(C)CN1C1=CC=C(C(=O)NC=2C=C(NC(=O)C=3C=CC=CC=3)C(Cl)=CC=2)C=N1 DFEYDQWPGMZDLB-UHFFFAOYSA-N 0.000 claims 1
- ITHVXQZFZHIJJQ-UHFFFAOYSA-N n-(3-benzamido-4-chlorophenyl)-6-(4-ethylpiperazin-1-yl)pyridine-3-carboxamide Chemical compound C1CN(CC)CCN1C1=CC=C(C(=O)NC=2C=C(NC(=O)C=3C=CC=CC=3)C(Cl)=CC=2)C=N1 ITHVXQZFZHIJJQ-UHFFFAOYSA-N 0.000 claims 1
- YRDRSANPYBSCDM-UHFFFAOYSA-N n-(3-benzamido-4-chlorophenyl)-6-(4-hydroxypiperidin-1-yl)pyridine-3-carboxamide Chemical compound C1CC(O)CCN1C1=CC=C(C(=O)NC=2C=C(NC(=O)C=3C=CC=CC=3)C(Cl)=CC=2)C=N1 YRDRSANPYBSCDM-UHFFFAOYSA-N 0.000 claims 1
- BUMIPXWMQKBXQR-UHFFFAOYSA-N n-(3-benzamido-4-chlorophenyl)-6-(bromomethyl)pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=CC=CC=2)C(Cl)=CC=C1NC(=O)C1=CC=C(CBr)N=C1 BUMIPXWMQKBXQR-UHFFFAOYSA-N 0.000 claims 1
- VVMXHQMUPPNVAV-UHFFFAOYSA-N n-(3-benzamido-4-chlorophenyl)-6-(morpholin-4-ylmethyl)pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=CC=CC=2)C(Cl)=CC=C1NC(=O)C(C=N1)=CC=C1CN1CCOCC1 VVMXHQMUPPNVAV-UHFFFAOYSA-N 0.000 claims 1
- LEWRNCNLOPGICI-UHFFFAOYSA-N n-(3-benzamido-4-chlorophenyl)-6-(piperidin-1-ylmethyl)pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=CC=CC=2)C(Cl)=CC=C1NC(=O)C(C=N1)=CC=C1CN1CCCCC1 LEWRNCNLOPGICI-UHFFFAOYSA-N 0.000 claims 1
- DFEYDQWPGMZDLB-MRXNPFEDSA-N n-(3-benzamido-4-chlorophenyl)-6-[(3r)-3-methylpiperazin-1-yl]pyridine-3-carboxamide Chemical compound C1CN[C@H](C)CN1C1=CC=C(C(=O)NC=2C=C(NC(=O)C=3C=CC=CC=3)C(Cl)=CC=2)C=N1 DFEYDQWPGMZDLB-MRXNPFEDSA-N 0.000 claims 1
- QEEUJJAERGNXCX-CALCHBBNSA-N n-(3-benzamido-4-chlorophenyl)-6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-2-methylpyridine-3-carboxamide Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1C)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C=CC=CC=2)=C1 QEEUJJAERGNXCX-CALCHBBNSA-N 0.000 claims 1
- MDHDXACOTZFIHY-UHFFFAOYSA-N n-(3-benzamido-4-chlorophenyl)-6-chloro-2-methylpyridine-3-carboxamide Chemical compound CC1=NC(Cl)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C=CC=CC=2)=C1 MDHDXACOTZFIHY-UHFFFAOYSA-N 0.000 claims 1
- NHIBDGLYFWBTSK-UHFFFAOYSA-N n-(3-benzamido-4-chlorophenyl)-6-chloropyridine-3-carboxamide Chemical compound C1=NC(Cl)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C=CC=CC=2)=C1 NHIBDGLYFWBTSK-UHFFFAOYSA-N 0.000 claims 1
- VURIHKMGNGBSFS-UHFFFAOYSA-N n-(3-benzamido-4-chlorophenyl)-6-morpholin-4-ylpyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=CC=CC=2)C(Cl)=CC=C1NC(=O)C(C=N1)=CC=C1N1CCOCC1 VURIHKMGNGBSFS-UHFFFAOYSA-N 0.000 claims 1
- NZAFWXTXBBQYOI-UHFFFAOYSA-N n-[2-chloro-5-[(2-chloro-4-methylsulfonylbenzoyl)amino]phenyl]pyridine-3-carboxamide Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C=NC=CC=2)=C1 NZAFWXTXBBQYOI-UHFFFAOYSA-N 0.000 claims 1
- HYJAVMNLXZERBM-UHFFFAOYSA-N n-[2-chloro-5-[[4-(methylsulfonylmethyl)benzoyl]amino]phenyl]pyridine-3-carboxamide Chemical compound C1=CC(CS(=O)(=O)C)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C=NC=CC=2)=C1 HYJAVMNLXZERBM-UHFFFAOYSA-N 0.000 claims 1
- MZAFYYXTZZVKKP-UHFFFAOYSA-N n-[4-chloro-3-[(2-chlorobenzoyl)amino]phenyl]-2-methyl-6-(trifluoromethyl)pyridine-3-carboxamide Chemical compound CC1=NC(C(F)(F)F)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C(=CC=CC=2)Cl)=C1 MZAFYYXTZZVKKP-UHFFFAOYSA-N 0.000 claims 1
- CSFAEEBDMGKDKY-UHFFFAOYSA-N n-[4-chloro-3-[(2-morpholin-4-ylbenzoyl)amino]phenyl]-2-methyl-6-(trifluoromethyl)pyridine-3-carboxamide Chemical compound CC1=NC(C(F)(F)F)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C(=CC=CC=2)N2CCOCC2)=C1 CSFAEEBDMGKDKY-UHFFFAOYSA-N 0.000 claims 1
- TZCSEURJEIFSFX-UHFFFAOYSA-N n-[4-chloro-3-[(3-chloro-4-fluorobenzoyl)amino]phenyl]-2-methyl-6-(trifluoromethyl)pyridine-3-carboxamide Chemical compound CC1=NC(C(F)(F)F)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C=C(Cl)C(F)=CC=2)=C1 TZCSEURJEIFSFX-UHFFFAOYSA-N 0.000 claims 1
- YVGZPZQXOQYOKL-UHFFFAOYSA-N n-[4-chloro-3-[(3-fluorobenzoyl)amino]phenyl]-2-methyl-6-(trifluoromethyl)pyridine-3-carboxamide Chemical compound CC1=NC(C(F)(F)F)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C=C(F)C=CC=2)=C1 YVGZPZQXOQYOKL-UHFFFAOYSA-N 0.000 claims 1
- VPPUAPPRJHCBQG-UHFFFAOYSA-N n-[4-chloro-3-[(4-fluorobenzoyl)amino]phenyl]-2-methyl-6-(trifluoromethyl)pyridine-3-carboxamide Chemical compound CC1=NC(C(F)(F)F)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C=CC(F)=CC=2)=C1 VPPUAPPRJHCBQG-UHFFFAOYSA-N 0.000 claims 1
- RHQAOPKNHZGBEW-UHFFFAOYSA-N n-[4-chloro-3-[(4-fluorobenzoyl)amino]phenyl]-6-(3,5-dimethylpiperazin-1-yl)-2-methylpyridine-3-carboxamide Chemical compound C1C(C)NC(C)CN1C(N=C1C)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C=CC(F)=CC=2)=C1 RHQAOPKNHZGBEW-UHFFFAOYSA-N 0.000 claims 1
- LOWXYZOZNHDYCY-UHFFFAOYSA-N n-[4-chloro-3-[(4-fluorobenzoyl)amino]phenyl]-6-(3-methylpiperazin-1-yl)pyridine-3-carboxamide Chemical compound C1CNC(C)CN1C1=CC=C(C(=O)NC=2C=C(NC(=O)C=3C=CC(F)=CC=3)C(Cl)=CC=2)C=N1 LOWXYZOZNHDYCY-UHFFFAOYSA-N 0.000 claims 1
- LYEDMYINSIGZMX-UHFFFAOYSA-N n-[4-chloro-3-[(4-fluorobenzoyl)amino]phenyl]-6-(4-ethylpiperazin-1-yl)pyridine-3-carboxamide Chemical compound C1CN(CC)CCN1C1=CC=C(C(=O)NC=2C=C(NC(=O)C=3C=CC(F)=CC=3)C(Cl)=CC=2)C=N1 LYEDMYINSIGZMX-UHFFFAOYSA-N 0.000 claims 1
- QHMXHWIUCJYTHQ-UHFFFAOYSA-N n-[4-chloro-3-[(4-fluorobenzoyl)amino]phenyl]-6-(4-hydroxypiperidin-1-yl)-2-methylpyridine-3-carboxamide Chemical compound CC1=NC(N2CCC(O)CC2)=CC=C1C(=O)NC(C=1)=CC=C(Cl)C=1NC(=O)C1=CC=C(F)C=C1 QHMXHWIUCJYTHQ-UHFFFAOYSA-N 0.000 claims 1
- YBHUUTWVUYPKFU-UHFFFAOYSA-N n-[4-chloro-3-[(4-fluorobenzoyl)amino]phenyl]-6-(4-propanoylpiperazin-1-yl)pyridine-3-carboxamide Chemical compound C1CN(C(=O)CC)CCN1C1=CC=C(C(=O)NC=2C=C(NC(=O)C=3C=CC(F)=CC=3)C(Cl)=CC=2)C=N1 YBHUUTWVUYPKFU-UHFFFAOYSA-N 0.000 claims 1
- LOWXYZOZNHDYCY-OAHLLOKOSA-N n-[4-chloro-3-[(4-fluorobenzoyl)amino]phenyl]-6-[(3r)-3-methylpiperazin-1-yl]pyridine-3-carboxamide Chemical compound C1CN[C@H](C)CN1C1=CC=C(C(=O)NC=2C=C(NC(=O)C=3C=CC(F)=CC=3)C(Cl)=CC=2)C=N1 LOWXYZOZNHDYCY-OAHLLOKOSA-N 0.000 claims 1
- LOWXYZOZNHDYCY-HNNXBMFYSA-N n-[4-chloro-3-[(4-fluorobenzoyl)amino]phenyl]-6-[(3s)-3-methylpiperazin-1-yl]pyridine-3-carboxamide Chemical compound C1CN[C@@H](C)CN1C1=CC=C(C(=O)NC=2C=C(NC(=O)C=3C=CC(F)=CC=3)C(Cl)=CC=2)C=N1 LOWXYZOZNHDYCY-HNNXBMFYSA-N 0.000 claims 1
- AHQAGMIMLOHVOW-UHFFFAOYSA-N n-[4-chloro-3-[(4-fluorobenzoyl)amino]phenyl]-6-[4-(3-methylbutanoyl)piperazin-1-yl]pyridine-3-carboxamide Chemical compound C1CN(C(=O)CC(C)C)CCN1C1=CC=C(C(=O)NC=2C=C(NC(=O)C=3C=CC(F)=CC=3)C(Cl)=CC=2)C=N1 AHQAGMIMLOHVOW-UHFFFAOYSA-N 0.000 claims 1
- IRVGEFOZMIQFPH-UHFFFAOYSA-N n-[4-chloro-3-[(4-fluorobenzoyl)amino]phenyl]-6-piperazin-1-ylpyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1=CC(NC(=O)C=2C=NC(=CC=2)N2CCNCC2)=CC=C1Cl IRVGEFOZMIQFPH-UHFFFAOYSA-N 0.000 claims 1
- XFURFBDPQZTLLR-UHFFFAOYSA-N n-[4-chloro-3-[[4-(4-methylpiperazin-1-yl)benzoyl]amino]phenyl]-2-methyl-6-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1CN(C)CCN1C1=CC=C(C(=O)NC=2C(=CC=C(NC(=O)C=3C(=NC(=CC=3)C(F)(F)F)C)C=2)Cl)C=C1 XFURFBDPQZTLLR-UHFFFAOYSA-N 0.000 claims 1
- UOUNRTOARYWRRE-UHFFFAOYSA-N n-[4-chloro-3-[[4-(thiadiazol-4-yl)benzoyl]amino]phenyl]-2-methyl-6-(trifluoromethyl)pyridine-3-carboxamide Chemical compound CC1=NC(C(F)(F)F)=CC=C1C(=O)NC1=CC=C(Cl)C(NC(=O)C=2C=CC(=CC=2)C=2N=NSC=2)=C1 UOUNRTOARYWRRE-UHFFFAOYSA-N 0.000 claims 1
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| DK2137162T3 (en) * | 2007-03-15 | 2018-11-26 | Novartis Ag | Organic compounds and their applications |
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| US20100041663A1 (en) * | 2008-07-18 | 2010-02-18 | Novartis Ag | Organic Compounds as Smo Inhibitors |
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| RU2754507C2 (ru) | 2016-06-24 | 2021-09-02 | Инфинити Фармасьютикалз, Инк. | Комбинированная терапия |
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| RU2721421C2 (ru) * | 2018-08-06 | 2020-05-19 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Производное бисамидов дикарбоновых кислот, его применение, фармацевтическая композиция на его основе, способы его получения |
| RU2709529C1 (ru) * | 2018-08-06 | 2019-12-18 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Производные бисамидов дикарбоновых кислот, их применение, фармацевтическая композиция на их основе, способы их получения |
| RU2725770C2 (ru) * | 2018-08-06 | 2020-07-07 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Производное бисамидов дикарбоновых кислот, его применение, фармацевтическая композиция на его основе, способы его получения |
| RU2725881C2 (ru) * | 2018-08-06 | 2020-07-07 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Производное бисамидов дикарбоновых кислот, его применение, фармацевтическая композиция на его основе, способы его получения |
| WO2021241913A1 (ko) * | 2020-05-29 | 2021-12-02 | 주식회사 헤지호그 | 페닐렌 디벤즈아미드계 화합물 및 이를 유효성분으로 포함하는 암질환 예방 또는 치료용 약제학적 조성물 |
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| GB9623833D0 (en) * | 1996-11-16 | 1997-01-08 | Zeneca Ltd | Chemical compound |
| ES2188005T3 (es) * | 1997-09-23 | 2003-06-16 | Astrazeneca Ab | Derivados de amidas para el tratamiento de enfermedades mediadas por citoquinas. |
| JP2003505337A (ja) * | 1998-05-15 | 2003-02-12 | アストラゼネカ アクチボラグ | サイトカインにより仲介される疾病を処置するためのベンズアミド誘導体 |
| US6432949B1 (en) * | 1998-08-04 | 2002-08-13 | Astrazeneca Ab | Amide derivatives useful as inhibitors of the production of cytokines |
| EP1115707B1 (en) | 1998-09-25 | 2003-11-12 | AstraZeneca AB | Benzamide derivatives and ther use as cytokine inhibitors |
| ME00275B (me) | 1999-01-13 | 2011-02-10 | Bayer Corp | ω-KARBOKSIARIL SUPSTITUISANI DIFENIL KARBAMIDI KAO INHIBITORI RAF KINAZE |
| US7202257B2 (en) | 2003-12-24 | 2007-04-10 | Deciphera Pharmaceuticals, Llc | Anti-inflammatory medicaments |
| WO2005033288A2 (en) * | 2003-09-29 | 2005-04-14 | The Johns Hopkins University | Hedgehog pathway antagonists |
| WO2006007520A1 (en) * | 2004-07-01 | 2006-01-19 | Wisconsin Alumni Research Foundation | Hydroxybenazamide compounds for treatment of cancer |
| TW200616974A (en) * | 2004-07-01 | 2006-06-01 | Astrazeneca Ab | Chemical compounds |
| AU2005278961A1 (en) * | 2004-09-01 | 2006-03-09 | Astrazeneca Ab | Quinazolinone derivatives and their use as B-Raf inhibitors |
| JP2008516939A (ja) * | 2004-10-15 | 2008-05-22 | アストラゼネカ アクチボラグ | 化学化合物 |
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