JP2009516685A5 - - Google Patents
Download PDFInfo
- 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
Links
- -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
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 230000037361 pathway Effects 0.000 claims 1
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims 1
- 230000011664 signaling Effects 0.000 claims 1
- 210000003699 striated muscle Anatomy 0.000 claims 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73586105P | 2005-11-14 | 2005-11-14 | |
| US60/735,861 | 2005-11-14 | ||
| PCT/US2006/044240 WO2007059157A1 (en) | 2005-11-14 | 2006-11-14 | Bisamide inhibitors of hedgehog signaling |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013005689A Division JP2013079283A (ja) | 2005-11-14 | 2013-01-16 | ヘッジホッグシグナル伝達のビスアミド阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009516685A JP2009516685A (ja) | 2009-04-23 |
| JP2009516685A5 true JP2009516685A5 (enExample) | 2010-01-14 |
| JP5225857B2 JP5225857B2 (ja) | 2013-07-03 |
Family
ID=37734100
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008541289A Expired - Fee Related JP5225857B2 (ja) | 2005-11-14 | 2006-11-14 | ヘッジホッグシグナル伝達のビスアミド阻害剤 |
| JP2013005689A Pending JP2013079283A (ja) | 2005-11-14 | 2013-01-16 | ヘッジホッグシグナル伝達のビスアミド阻害剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013005689A Pending JP2013079283A (ja) | 2005-11-14 | 2013-01-16 | ヘッジホッグシグナル伝達のビスアミド阻害剤 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8101610B2 (enExample) |
| EP (1) | EP1957461B1 (enExample) |
| JP (2) | JP5225857B2 (enExample) |
| AU (1) | AU2006315467B2 (enExample) |
| CA (1) | CA2629814C (enExample) |
| DK (1) | DK1957461T3 (enExample) |
| ES (1) | ES2604539T3 (enExample) |
| WO (1) | WO2007059157A1 (enExample) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI433674B (zh) | 2006-12-28 | 2014-04-11 | Infinity Discovery Inc | 環杷明（ｃｙｃｌｏｐａｍｉｎｅ）類似物類 |
| US8536168B2 (en) * | 2007-03-15 | 2013-09-17 | Novartis Ag | Benzyl and pyridinyl derivatives as modulators of the hedgehog signaling pathway |
| WO2009086451A1 (en) | 2007-12-27 | 2009-07-09 | Infinity Pharmaceuticals, Inc. | Methods for stereoselective reduction |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| US20100041663A1 (en) | 2008-07-18 | 2010-02-18 | Novartis Ag | Organic Compounds as Smo Inhibitors |
| FR2948367A1 (fr) | 2009-07-24 | 2011-01-28 | Centre Nat Rech Scient | Derives d'acyl-guanidines modulateurs de la voie de signalisation des proteines hedgehog |
| WO2011014888A1 (en) * | 2009-07-31 | 2011-02-03 | Selexagen Therapeutics | Novel hedgehog inhibitors |
| CA2769795C (en) | 2009-08-05 | 2020-01-07 | Infinity Pharmaceuticals, Inc. | Enzymatic transamination of cyclopamine analogs |
| JP5887270B2 (ja) * | 2009-09-02 | 2016-03-16 | ジェネンテック， インコーポレイテッド | 突然変異体ｓｍｏｏｔｈｅｎｅｄおよびその使用方法 |
| JP2013516480A (ja) | 2010-01-07 | 2013-05-13 | セレクサゲン セラピューティクス，インク． | ヘッジホッグ阻害剤 |
| JP5951600B2 (ja) | 2010-05-21 | 2016-07-13 | インフィニティー ファーマシューティカルズ， インコーポレイテッド | キナーゼ調節のための、化合物、組成物および方法 |
| US9376447B2 (en) | 2010-09-14 | 2016-06-28 | Infinity Pharmaceuticals, Inc. | Transfer hydrogenation of cyclopamine analogs |
| US8481680B2 (en) | 2010-10-05 | 2013-07-09 | Genentech, Inc. | Mutant smoothened and methods of using the same |
| WO2012064973A2 (en) | 2010-11-10 | 2012-05-18 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| FR2967498B1 (fr) | 2010-11-16 | 2015-01-02 | Centre Nat Rech Scient | Utilisation de derives de quinolinone comme outil de recherche |
| US9708299B2 (en) | 2011-01-03 | 2017-07-18 | Genentech, Inc. | Hedgehog antagonists having zinc binding moieties |
| EP3238722B1 (en) | 2011-01-10 | 2019-03-13 | Infinity Pharmaceuticals, Inc. | Solid forms of isoquinolinones |
| WO2012151544A1 (en) | 2011-05-05 | 2012-11-08 | Wisconsin Alumni Research Foundation | Micelles for the solubilization of gossypol |
| EP2734520B1 (en) | 2011-07-19 | 2016-09-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| US9056877B2 (en) | 2011-07-19 | 2015-06-16 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| PE20141371A1 (es) | 2011-08-29 | 2014-10-13 | Infinity Pharmaceuticals Inc | Compuestos heterociclicos y usos de los mismos |
| FR2980477B1 (fr) | 2011-09-23 | 2013-10-18 | Centre Nat Rech Scient | Nouveaux composes modulateurs de la voie de signalisation des proteines hedgehog, leurs formes marquees, et applications |
| US9630979B2 (en) | 2011-09-29 | 2017-04-25 | Infinity Pharmaceuticals, Inc. | Inhibitors of monoacylglycerol lipase and methods of their use |
| US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| JP6233932B2 (ja) | 2012-08-30 | 2017-11-22 | 国立大学法人広島大学 | ＢＢＦ２Ｈ７（ＢＢＦ２ ｈｕｍａｎ ｈｏｍｏｌｏｇｕｅ ｏｎ ｃｈｒｏｍｏｓｏｍｅ７）部分アミノ酸配列を有するペプチドまたはそれに結合する抗体を含む細胞増殖調節用組成物 |
| CA2878082A1 (en) * | 2012-09-17 | 2014-03-20 | Duke University | Smoothened modulators and methods of use thereof |
| RU2702908C2 (ru) | 2012-11-01 | 2019-10-14 | Инфинити Фармасьютикалз, Инк. | Лечение злокачественных опухолей с использованием модуляторов изоформ pi3-киназы |
| EP2914592B1 (en) | 2012-11-03 | 2017-10-11 | Boehringer Ingelheim International GmbH | Inhibitors of cytomegalovirus |
| EP2925363A4 (en) | 2012-11-29 | 2016-11-09 | Strasspharma Llc | METHOD FOR MODULATING FOLLICLE-STIMULATING HORMONACTIVITY |
| NZ629037A (en) | 2013-03-15 | 2017-04-28 | Infinity Pharmaceuticals Inc | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
| RU2665688C2 (ru) * | 2013-04-12 | 2018-09-04 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Производные бисамидов дикарбоновых кислот, их применение, фармацевтическая композиция на их основе, способы их получения |
| US9192609B2 (en) | 2013-04-17 | 2015-11-24 | Hedgepath Pharmaceuticals, Inc. | Treatment and prognostic monitoring of proliferation disorders using hedgehog pathway inhibitors |
| KR20160013204A (ko) | 2013-05-30 | 2016-02-03 | 인피니티 파마슈티칼스, 인코포레이티드 | Pi3 키나아제 동형단백질 조절제를 사용하는 암의 치료 |
| EP3964507A1 (en) | 2013-10-04 | 2022-03-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| GB201317609D0 (en) | 2013-10-04 | 2013-11-20 | Cancer Rec Tech Ltd | Inhibitor compounds |
| WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| US20160244452A1 (en) | 2013-10-21 | 2016-08-25 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| USRE50030E1 (en) | 2013-12-13 | 2024-07-02 | Dana-Farber Cancer Institute, Inc. | Methods to treat lymphoplasmacytic lymphoma |
| EP3079682A4 (en) * | 2013-12-13 | 2017-08-30 | Dana-Farber Cancer Institute, Inc. | Methods to treat lymphoplasmacytic lymphoma |
| US20170044232A1 (en) | 2014-02-04 | 2017-02-16 | Genentech, Inc. | Mutant smoothened and methods of using the same |
| CN106456628A (zh) | 2014-03-19 | 2017-02-22 | 无限药品股份有限公司 | 用于治疗PI3K‑γ介导的障碍的杂环化合物 |
| US20150320754A1 (en) | 2014-04-16 | 2015-11-12 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| WO2015168079A1 (en) | 2014-04-29 | 2015-11-05 | Infinity Pharmaceuticals, Inc. | Pyrimidine or pyridine derivatives useful as pi3k inhibitors |
| WO2016054491A1 (en) | 2014-10-03 | 2016-04-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CA2965178C (en) | 2014-10-22 | 2023-09-26 | Dana-Farber Cancer Institute, Inc. | Thiazolyl-containing compounds for treating proliferative diseases |
| CN107636170A (zh) | 2015-02-04 | 2018-01-26 | 健泰科生物技术公司 | 突变型Smoothened及其使用方法 |
| GB201505658D0 (en) | 2015-04-01 | 2015-05-13 | Cancer Rec Tech Ltd | Inhibitor compounds |
| CN104876879B (zh) * | 2015-04-14 | 2018-05-18 | 中国科学院合肥物质科学研究院 | 一种bcr-abl激酶抑制剂 |
| BR112017026103B1 (pt) | 2015-06-04 | 2023-10-03 | Sol-Gel Technologies Ltd | Composições tópicas com composto inibidor de hedgehog, sistema de entrega tópica e seus usos |
| CN114230571B (zh) | 2015-09-14 | 2025-07-08 | 无限药品股份有限公司 | 异喹啉酮的固体形式、其制备方法、包含其的组合物及其使用方法 |
| US20170231968A1 (en) | 2016-02-11 | 2017-08-17 | PellePharm, Inc. | Method for relief of and treatment of pruritus |
| US10919914B2 (en) | 2016-06-08 | 2021-02-16 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| EP3474856B1 (en) | 2016-06-24 | 2022-09-14 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| US10548908B2 (en) * | 2016-09-15 | 2020-02-04 | Nostopharma, LLC | Compositions and methods for preventing and treating heterotopic ossification and pathologic calcification |
| GB201617103D0 (en) | 2016-10-07 | 2016-11-23 | Cancer Research Technology Limited | Compound |
| 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 |
| 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 |
| 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 |
| 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 |
| WO2021241913A1 (ko) * | 2020-05-29 | 2021-12-02 | 주식회사 헤지호그 | 페닐렌 디벤즈아미드계 화합물 및 이를 유효성분으로 포함하는 암질환 예방 또는 치료용 약제학적 조성물 |
| EP4185279A4 (en) | 2020-07-24 | 2024-05-01 | Secura Bio, Inc. | TREATING CANCER WITH PI3-KINASE ISOFORM MODULATORS |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9623833D0 (en) * | 1996-11-16 | 1997-01-08 | Zeneca Ltd | Chemical compound |
| DK1017378T3 (da) * | 1997-09-23 | 2003-03-17 | Astrazeneca Ab | Amidderivater til behandling af sygdomme medieret af cytokiner |
| IL139710A (en) * | 1998-05-15 | 2005-07-25 | Astazeneca Ab | Benzamide derivatives for the treatment of diseases mediated by cytokines |
| BR9912729A (pt) * | 1998-08-04 | 2001-05-02 | Astrazeneca Ab | Derivado de amida, processo para prepará-lo, e, uso do mesmo |
| ATE254105T1 (de) * | 1998-09-25 | 2003-11-15 | Astrazeneca Ab | Benzamid-derivate und ihre verwendung als cytokine inhibitoren |
| US7351834B1 (en) * | 1999-01-13 | 2008-04-01 | Bayer Pharmaceuticals Corporation | ω-Carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| 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 |
| TW200616974A (en) * | 2004-07-01 | 2006-06-01 | Astrazeneca Ab | Chemical compounds |
| WO2006007520A1 (en) | 2004-07-01 | 2006-01-19 | Wisconsin Alumni Research Foundation | Hydroxybenazamide compounds for treatment of cancer |
| AU2005278961A1 (en) | 2004-09-01 | 2006-03-09 | Astrazeneca Ab | Quinazolinone derivatives and their use as B-Raf inhibitors |
| CA2583096A1 (en) * | 2004-10-15 | 2006-04-20 | Astrazeneca Ab | Quinoxalines as b raf inhibitors |
-
2006
- 2006-11-14 EP EP06844364.7A patent/EP1957461B1/en active Active
- 2006-11-14 CA CA2629814A patent/CA2629814C/en not_active Expired - Fee Related
- 2006-11-14 DK DK06844364.7T patent/DK1957461T3/en active
- 2006-11-14 JP JP2008541289A patent/JP5225857B2/ja not_active Expired - Fee Related
- 2006-11-14 ES ES06844364.7T patent/ES2604539T3/es active Active
- 2006-11-14 AU AU2006315467A patent/AU2006315467B2/en not_active Ceased
- 2006-11-14 WO PCT/US2006/044240 patent/WO2007059157A1/en not_active Ceased
- 2006-11-14 US US12/093,530 patent/US8101610B2/en not_active Expired - Fee Related
-
2013
- 2013-01-16 JP JP2013005689A patent/JP2013079283A/ja active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2462454C2 (ru) | Новое сульфонамидное производное малоновой кислоты и его фармацевтическое применение | |
| JP2016506964A5 (ja) | ナトリウムチャネルの調節剤としてのキノリンおよびキノキサリンアミド | |
| RU2423354C2 (ru) | Соединения и композиции - модуляторы сигнального пути hedgehog | |
| RU2217142C2 (ru) | Химические соединения | |
| RU2436780C2 (ru) | Производные 5-фенилтиазола и их применение в качестве ингибиторов рi3 киназы | |
| JP2012510989A5 (enExample) | ||
| RU2500673C2 (ru) | Гетероциклические ингибиторы мек и способы их применения | |
| RU2264389C2 (ru) | Азотсодержащие ароматические производные, их применение, лекарственное средство на их основе и способ лечения | |
| HRP20141190T1 (hr) | Disupstituirani derivati piridina kao antikancerogena sredstva | |
| JP2016513660A5 (enExample) | ||
| JP2019507179A5 (enExample) | ||
| JP2020502103A5 (enExample) | ||
| JP2020158523A (ja) | 新規ヒストンデアセチラーゼインヒビター | |
| JP2016508500A5 (enExample) | ||
| AU2006315467B2 (en) | Bisamide inhibitors of hedgehog signaling | |
| RU2003114740A (ru) | Азотсодержащие ароматические производные | |
| JP2020522520A5 (enExample) | ||
| JP2015531366A5 (enExample) | ||
| JP2008500284A5 (enExample) | ||
| RU2015122698A (ru) | Производное пиридина | |
| CA2536954A1 (en) | C-kit modulators and methods of use | |
| JP2010530438A5 (enExample) | ||
| RU2010110640A (ru) | Соединения и композиции 5-(4-(галогеналкокси)фенил)пиримидин-2-амина в качестве ингибиторов киназ | |
| RU2017121044A (ru) | Производные амидотиадиазола в качестве ингибиторов надфн-оксидазы | |
| JP2020520356A5 (enExample) |