JP2008524249A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008524249A5 JP2008524249A5 JP2007546990A JP2007546990A JP2008524249A5 JP 2008524249 A5 JP2008524249 A5 JP 2008524249A5 JP 2007546990 A JP2007546990 A JP 2007546990A JP 2007546990 A JP2007546990 A JP 2007546990A JP 2008524249 A5 JP2008524249 A5 JP 2008524249A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- amino
- amide
- carboxylic acid
- benzoxazol
- 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
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- -1 C 1 -C 4 alkyl Chemical group 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000003386 piperidinyl group Chemical group 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- GIBVENMRXKZTPM-UHFFFAOYSA-N 2-n-methyl-2-n-(1-methylpiperidin-4-yl)-1,3-benzoxazole-2,5-diamine Chemical compound N=1C2=CC(N)=CC=C2OC=1N(C)C1CCN(C)CC1 GIBVENMRXKZTPM-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 230000002496 gastric effect Effects 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- ZOUCZKGFQSOBPX-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-[2-[methyl-[(1-methylpyrrolidin-3-yl)methyl]amino]-1,3-benzothiazol-6-yl]prop-2-enamide Chemical compound N=1C2=CC=C(NC(=O)C=CC=3C=CC(F)=CC=3)C=C2SC=1N(C)CC1CCN(C)C1 ZOUCZKGFQSOBPX-UHFFFAOYSA-N 0.000 claims 1
- YEVSVQXTBWMTFO-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=CC(Cl)=C1Cl YEVSVQXTBWMTFO-UHFFFAOYSA-N 0.000 claims 1
- ONBXLEVZJQBTIT-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1Cl ONBXLEVZJQBTIT-UHFFFAOYSA-N 0.000 claims 1
- MYCDLACXMUBSAJ-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]benzamide Chemical compound C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1Cl MYCDLACXMUBSAJ-UHFFFAOYSA-N 0.000 claims 1
- STUCRICXTMRQCU-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-n-[2-[methyl-[(1-methylpyrrolidin-3-yl)methyl]amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C(=CC(Cl)=CC=3)Cl)=CC=C2OC=1N(C)CC1CCN(C)C1 STUCRICXTMRQCU-UHFFFAOYSA-N 0.000 claims 1
- OZFFPJBMCGKDGO-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(Cl)C=C1Cl OZFFPJBMCGKDGO-UHFFFAOYSA-N 0.000 claims 1
- LHKWCYAXJCSSSD-UHFFFAOYSA-N 4-(2,4-difluorophenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1F LHKWCYAXJCSSSD-UHFFFAOYSA-N 0.000 claims 1
- SUFQYLDLNPIWFA-UHFFFAOYSA-N 4-(2,4-difluorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C(=CC(F)=CC=3)F)=CC=C2OC=1N(C)C1CCN(C)CC1 SUFQYLDLNPIWFA-UHFFFAOYSA-N 0.000 claims 1
- FCTRGPBVBWWFEO-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1Cl FCTRGPBVBWWFEO-UHFFFAOYSA-N 0.000 claims 1
- ZFEFJGBXOJPMJV-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C(=CC(F)=CC=3)Cl)=CC=C2OC=1N(C)C1CCN(C)CC1 ZFEFJGBXOJPMJV-UHFFFAOYSA-N 0.000 claims 1
- GEYIMGZCBBHLLS-UHFFFAOYSA-N 4-(2-chloro-4-methoxyphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound ClC1=CC(OC)=CC=C1C1=CC=C(C(=O)NC=2C=C3SC(=NC3=CC=2)N(C)CCN(C)C)C=C1 GEYIMGZCBBHLLS-UHFFFAOYSA-N 0.000 claims 1
- VPVLGKHWGDSWOS-UHFFFAOYSA-N 4-(2-chloro-4-methoxyphenyl)-n-[2-[methyl-(1-methylpyrrolidin-3-yl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound ClC1=CC(OC)=CC=C1C1=CC=C(C(=O)NC=2C=C3SC(=NC3=CC=2)N(C)C2CN(C)CC2)C=C1 VPVLGKHWGDSWOS-UHFFFAOYSA-N 0.000 claims 1
- JUGMJUMMUIXDDH-UHFFFAOYSA-N 4-(2-chloro-4-methylphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(C)C=C1Cl JUGMJUMMUIXDDH-UHFFFAOYSA-N 0.000 claims 1
- SABVGGGSSMUCHU-UHFFFAOYSA-N 4-(2-chloro-4-methylphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]benzamide Chemical compound C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(C=C1)=CC=C1C1=CC=C(C)C=C1Cl SABVGGGSSMUCHU-UHFFFAOYSA-N 0.000 claims 1
- IMJSHZCHEKCMMO-UHFFFAOYSA-N 4-(2-chloro-4-methylphenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C(=CC(C)=CC=3)Cl)=CC=C2OC=1N(C)C1CCN(C)CC1 IMJSHZCHEKCMMO-UHFFFAOYSA-N 0.000 claims 1
- KLFMHWMYKHXPPX-UHFFFAOYSA-N 4-(2-chlorophenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=CC=C1Cl KLFMHWMYKHXPPX-UHFFFAOYSA-N 0.000 claims 1
- LZYQNYCOIAILLB-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1C LZYQNYCOIAILLB-UHFFFAOYSA-N 0.000 claims 1
- ZNIIXHHZSKDKNX-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]benzamide Chemical compound C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1C ZNIIXHHZSKDKNX-UHFFFAOYSA-N 0.000 claims 1
- ZPWCHBUCSRAAJV-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C(=CC(Cl)=CC=3)C)=CC=C2OC=1N(C)C1CCN(C)CC1 ZPWCHBUCSRAAJV-UHFFFAOYSA-N 0.000 claims 1
- RJPXKIYFULVOOL-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl(2-morpholin-4-ylethyl)amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)CCN1CCOCC1 RJPXKIYFULVOOL-UHFFFAOYSA-N 0.000 claims 1
- UVZCNFSHRBNSIZ-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl(2-piperidin-1-ylethyl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=C2SC=1N(C)CCN1CCCCC1 UVZCNFSHRBNSIZ-UHFFFAOYSA-N 0.000 claims 1
- RIACNWLBDGUXRR-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl(2-pyrrolidin-1-ylethyl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=C2SC=1N(C)CCN1CCCC1 RIACNWLBDGUXRR-UHFFFAOYSA-N 0.000 claims 1
- DTUTWRXCWDQXLW-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl(2-pyrrolidin-1-ylethyl)amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)CCN1CCCC1 DTUTWRXCWDQXLW-UHFFFAOYSA-N 0.000 claims 1
- DENUYBFZOWWZMD-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl(pyrrolidin-3-ylmethyl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=C2SC=1N(C)CC1CCNC1 DENUYBFZOWWZMD-UHFFFAOYSA-N 0.000 claims 1
- ZVUJSQKAGDBYOW-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-(1-methylpiperidin-3-yl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=C2SC=1N(C)C1CCCN(C)C1 ZVUJSQKAGDBYOW-UHFFFAOYSA-N 0.000 claims 1
- UYMHAJRALJBIPW-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-(1-methylpiperidin-3-yl)amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)C1CCCN(C)C1 UYMHAJRALJBIPW-UHFFFAOYSA-N 0.000 claims 1
- IZDIJERBVRWNHB-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=C2SC=1N(C)C1CCN(C)CC1 IZDIJERBVRWNHB-UHFFFAOYSA-N 0.000 claims 1
- ZKZAICOOMBXCAD-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 ZKZAICOOMBXCAD-UHFFFAOYSA-N 0.000 claims 1
- PFEVGHCXMYFBMG-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-(1-methylpyrrolidin-3-yl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=C2SC=1N(C)C1CCN(C)C1 PFEVGHCXMYFBMG-UHFFFAOYSA-N 0.000 claims 1
- AEFQFYCFMSYGIW-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-[(1-methylpyrrolidin-3-yl)methyl]amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=C2SC=1N(C)CC1CCN(C)C1 AEFQFYCFMSYGIW-UHFFFAOYSA-N 0.000 claims 1
- HZXNSRKYOLVDLC-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-[(1-methylpyrrolidin-3-yl)methyl]amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)CC1CCN(C)C1 HZXNSRKYOLVDLC-UHFFFAOYSA-N 0.000 claims 1
- HYBZZXNHVCSXTD-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-[(1-propan-2-ylpyrrolidin-3-yl)methyl]amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1N(C(C)C)CCC1CN(C)C(SC1=C2)=NC1=CC=C2NC(=O)C1=CC=C(C=2C=CC(F)=CC=2)C=C1 HYBZZXNHVCSXTD-UHFFFAOYSA-N 0.000 claims 1
- YCMLBMBFGGTDJG-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-[(4-methylmorpholin-2-yl)methyl]amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)CC1CN(C)CCO1 YCMLBMBFGGTDJG-UHFFFAOYSA-N 0.000 claims 1
- ZOXJDUXHJQLQSQ-UHFFFAOYSA-N 4-(cyclohexylmethoxy)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]benzamide Chemical compound C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(C=C1)=CC=C1OCC1CCCCC1 ZOXJDUXHJQLQSQ-UHFFFAOYSA-N 0.000 claims 1
- PVZKHGCZCWBUFT-UHFFFAOYSA-N 4-(cyclohexylmethoxy)-n-[2-[methyl-(1-methylpyrrolidin-3-yl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(OCC4CCCCC4)=CC=3)C=C2SC=1N(C)C1CCN(C)C1 PVZKHGCZCWBUFT-UHFFFAOYSA-N 0.000 claims 1
- YXKFVWASWPAUPW-UHFFFAOYSA-N 4-[2-chloro-4-(trifluoromethoxy)phenyl]-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1Cl YXKFVWASWPAUPW-UHFFFAOYSA-N 0.000 claims 1
- NKIOIHGLSSJCCL-UHFFFAOYSA-N 4-[2-chloro-4-(trifluoromethyl)phenyl]-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1Cl NKIOIHGLSSJCCL-UHFFFAOYSA-N 0.000 claims 1
- LSRPRFQIHPWLLJ-UHFFFAOYSA-N 4-butyl-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]benzamide Chemical compound C1=CC(CCCC)=CC=C1C(=O)NC1=CC=C(OC(=N2)N(C)CCN(C)C)C2=C1 LSRPRFQIHPWLLJ-UHFFFAOYSA-N 0.000 claims 1
- IOZTWPVHQPXZIB-UHFFFAOYSA-N 4-butyl-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound C1=CC(CCCC)=CC=C1C(=O)NC1=CC=C(OC(=N2)N(C)C3CCN(C)CC3)C2=C1 IOZTWPVHQPXZIB-UHFFFAOYSA-N 0.000 claims 1
- ZHXWJURUCGVVNP-UHFFFAOYSA-N 4-cyclohexyl-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1CCCCC1 ZHXWJURUCGVVNP-UHFFFAOYSA-N 0.000 claims 1
- RBUXIZRDHUTKLX-UHFFFAOYSA-N 4-cyclohexyl-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]benzamide Chemical compound C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(C=C1)=CC=C1C1CCCCC1 RBUXIZRDHUTKLX-UHFFFAOYSA-N 0.000 claims 1
- MHLZYUDQMAURHU-UHFFFAOYSA-N 4-cyclohexyl-n-[2-[3-(dimethylamino)propyl-methylamino]-1,3-benzoxazol-5-yl]benzamide Chemical compound C=1C=C2OC(N(C)CCCN(C)C)=NC2=CC=1NC(=O)C(C=C1)=CC=C1C1CCCCC1 MHLZYUDQMAURHU-UHFFFAOYSA-N 0.000 claims 1
- GQSGWVSFLDDCQL-UHFFFAOYSA-N 4-cyclohexyl-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C3CCCCC3)=CC=C2OC=1N(C)C1CCN(C)CC1 GQSGWVSFLDDCQL-UHFFFAOYSA-N 0.000 claims 1
- FQSXZROVGPLTIC-UHFFFAOYSA-N 4-cyclohexyl-n-[2-[methyl-[(1-methylpyrrolidin-3-yl)methyl]amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C3CCCCC3)=CC=C2OC=1N(C)CC1CCN(C)C1 FQSXZROVGPLTIC-UHFFFAOYSA-N 0.000 claims 1
- HQVFLHIVNFRORQ-UHFFFAOYSA-N 4-cyclohexyloxy-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1OC1CCCCC1 HQVFLHIVNFRORQ-UHFFFAOYSA-N 0.000 claims 1
- GYQUEDMRCRSIFG-UHFFFAOYSA-N 4-cyclohexyloxy-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]benzamide Chemical compound C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(C=C1)=CC=C1OC1CCCCC1 GYQUEDMRCRSIFG-UHFFFAOYSA-N 0.000 claims 1
- SVFIPJLEPHBEDN-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]thiophene-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3SC(=CC=3)C=3C=C4OCOC4=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 SVFIPJLEPHBEDN-UHFFFAOYSA-N 0.000 claims 1
- RQFTVLJJTFOTGR-UHFFFAOYSA-N 5-(2,4-difluorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]thiophene-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3SC(=CC=3)C=3C(=CC(F)=CC=3)F)=CC=C2OC=1N(C)C1CCN(C)CC1 RQFTVLJJTFOTGR-UHFFFAOYSA-N 0.000 claims 1
- NBXILYIJACTNDG-UHFFFAOYSA-N 5-(3,4-difluorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]thiophene-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3SC(=CC=3)C=3C=C(F)C(F)=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 NBXILYIJACTNDG-UHFFFAOYSA-N 0.000 claims 1
- UMOPRZIUHFFBEN-UHFFFAOYSA-N 5-(3-chlorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]thiophene-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3SC(=CC=3)C=3C=C(Cl)C=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 UMOPRZIUHFFBEN-UHFFFAOYSA-N 0.000 claims 1
- ZZVWDOFDAVXTIS-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]thiophene-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3SC(=CC=3)C=3C=CC(Cl)=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 ZZVWDOFDAVXTIS-UHFFFAOYSA-N 0.000 claims 1
- ZMNNARNHHOQVNW-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]pyrazine-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3N=CC(=NC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 ZMNNARNHHOQVNW-UHFFFAOYSA-N 0.000 claims 1
- KDNFSIYGFOKCPG-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]thiophene-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3SC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 KDNFSIYGFOKCPG-UHFFFAOYSA-N 0.000 claims 1
- BRTSOBBUFALQCT-UHFFFAOYSA-N 5-(4-methoxyphenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]thiophene-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(=O)NC=2C=C3N=C(OC3=CC=2)N(C)C2CCN(C)CC2)S1 BRTSOBBUFALQCT-UHFFFAOYSA-N 0.000 claims 1
- OHEOLKHLDJYUCZ-UHFFFAOYSA-N 5-(5-chlorothiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(Cl)S1 OHEOLKHLDJYUCZ-UHFFFAOYSA-N 0.000 claims 1
- NUZWQKDXTFZYAX-UHFFFAOYSA-N 5-thiophen-3-ylthiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CSC=C1 NUZWQKDXTFZYAX-UHFFFAOYSA-N 0.000 claims 1
- ZUCVJIIRYGCSCT-UHFFFAOYSA-N 6-(4-fluorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]pyridine-3-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3C=NC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 ZUCVJIIRYGCSCT-UHFFFAOYSA-N 0.000 claims 1
- ZALQSURZVFZOEZ-UHFFFAOYSA-N 6-(4-fluorophenyl)-n-[2-[methyl-[(1-methylpyrrolidin-3-yl)methyl]amino]-1,3-benzoxazol-5-yl]pyridine-3-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3C=NC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)CC1CCN(C)C1 ZALQSURZVFZOEZ-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 206010003211 Arteriosclerosis coronary artery Diseases 0.000 claims 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010011224 Cough Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 208000007882 Gastritis Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010022714 Intestinal ulcer Diseases 0.000 claims 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N Methylcyclohexane Natural products CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims 1
- 208000007920 Neurogenic Inflammation Diseases 0.000 claims 1
- 208000000693 Neurogenic Urinary Bladder Diseases 0.000 claims 1
- 206010029279 Neurogenic bladder Diseases 0.000 claims 1
- 206010030216 Oesophagitis Diseases 0.000 claims 1
- 208000008469 Peptic Ulcer Diseases 0.000 claims 1
- 206010036774 Proctitis Diseases 0.000 claims 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 208000026758 coronary atherosclerosis Diseases 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 238000013016 damping Methods 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000002183 duodenal effect Effects 0.000 claims 1
- 230000004406 elevated intraocular pressure Effects 0.000 claims 1
- 208000006881 esophagitis Diseases 0.000 claims 1
- 201000001421 hyperglycemia Diseases 0.000 claims 1
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims 1
- 230000004899 motility Effects 0.000 claims 1
- IKUCMRISMDTNMJ-UHFFFAOYSA-N n-[2-[(1-ethylpyrrolidin-3-yl)methyl-methylamino]-1,3-benzothiazol-6-yl]-4-(4-fluorophenyl)benzamide Chemical compound C1N(CC)CCC1CN(C)C(SC1=C2)=NC1=CC=C2NC(=O)C1=CC=C(C=2C=CC(F)=CC=2)C=C1 IKUCMRISMDTNMJ-UHFFFAOYSA-N 0.000 claims 1
- IUVLNRPQZDDSDE-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-4-(2,4-dimethylphenyl)benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(C)C=C1C IUVLNRPQZDDSDE-UHFFFAOYSA-N 0.000 claims 1
- BSDHLTVXPGOMCF-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-4-(2-methylphenyl)benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=CC=C1C BSDHLTVXPGOMCF-UHFFFAOYSA-N 0.000 claims 1
- DXNJCJRPPBOPQU-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-4-(4-fluoro-2-methylphenyl)benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1C DXNJCJRPPBOPQU-UHFFFAOYSA-N 0.000 claims 1
- MJCKIPNEXQMFHC-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-4-(4-fluorophenyl)benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1 MJCKIPNEXQMFHC-UHFFFAOYSA-N 0.000 claims 1
- KFWKWURGAWHHAU-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]-4-(2-methylpropoxy)benzamide Chemical compound C1=CC(OCC(C)C)=CC=C1C(=O)NC1=CC=C(OC(=N2)N(C)CCN(C)C)C2=C1 KFWKWURGAWHHAU-UHFFFAOYSA-N 0.000 claims 1
- VDTOLZSLLBILOP-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]-4-(4-fluorophenyl)benzamide Chemical compound C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1 VDTOLZSLLBILOP-UHFFFAOYSA-N 0.000 claims 1
- ZEZZQXWBFHJPDJ-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]-4-phenoxybenzamide Chemical compound C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 ZEZZQXWBFHJPDJ-UHFFFAOYSA-N 0.000 claims 1
- LSWXUIKQWAVDOQ-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]-4-phenylbenzamide Chemical compound C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(C=C1)=CC=C1C1=CC=CC=C1 LSWXUIKQWAVDOQ-UHFFFAOYSA-N 0.000 claims 1
- PPALLMCFTWSXNB-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]-5-(4-fluorophenyl)pyrazine-2-carboxamide Chemical compound C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(N=C1)=CN=C1C1=CC=C(F)C=C1 PPALLMCFTWSXNB-UHFFFAOYSA-N 0.000 claims 1
- VOLWGJZOGHUICK-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]-6-(4-fluorophenyl)pyridine-3-carboxamide Chemical compound C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(C=N1)=CC=C1C1=CC=C(F)C=C1 VOLWGJZOGHUICK-UHFFFAOYSA-N 0.000 claims 1
- WQVXNSKERAVGRV-UHFFFAOYSA-N n-[2-[3-(diethylamino)propyl-methylamino]-1,3-benzothiazol-6-yl]-4-(4-fluorophenyl)benzamide Chemical compound C1=C2SC(N(C)CCCN(CC)CC)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1 WQVXNSKERAVGRV-UHFFFAOYSA-N 0.000 claims 1
- QHVUCRLWQPIHQK-UHFFFAOYSA-N n-[2-[3-(diethylamino)propyl-methylamino]-1,3-benzoxazol-5-yl]-4-(4-fluorophenyl)benzamide Chemical compound C=1C=C2OC(N(C)CCCN(CC)CC)=NC2=CC=1NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1 QHVUCRLWQPIHQK-UHFFFAOYSA-N 0.000 claims 1
- BFPQQVBJAMWCQD-UHFFFAOYSA-N n-[2-[methyl-(1-methylpiperidin-3-yl)amino]-1,3-benzoxazol-5-yl]-4-phenylbenzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C=CC=CC=3)=CC=C2OC=1N(C)C1CCCN(C)C1 BFPQQVBJAMWCQD-UHFFFAOYSA-N 0.000 claims 1
- TWNYZFKMAOXGSF-UHFFFAOYSA-N n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]-3-phenoxybenzamide Chemical compound N=1C2=CC(NC(=O)C=3C=C(OC=4C=CC=CC=4)C=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 TWNYZFKMAOXGSF-UHFFFAOYSA-N 0.000 claims 1
- ZEMSUXTVIFPYDJ-UHFFFAOYSA-N n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]-4-phenylbenzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C=CC=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 ZEMSUXTVIFPYDJ-UHFFFAOYSA-N 0.000 claims 1
- GSXMLQGRFQUXJQ-UHFFFAOYSA-N n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]-5-(4-methylphenyl)thiophene-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3SC(=CC=3)C=3C=CC(C)=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 GSXMLQGRFQUXJQ-UHFFFAOYSA-N 0.000 claims 1
- NSKWYDIZTDYCJX-UHFFFAOYSA-N n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]-5-phenylthiophene-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3SC(=CC=3)C=3C=CC=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 NSKWYDIZTDYCJX-UHFFFAOYSA-N 0.000 claims 1
- KYEKIAUYGKMCOK-UHFFFAOYSA-N n-[2-[methyl-[(1-methylpyrrolidin-3-yl)methyl]amino]-1,3-benzoxazol-5-yl]-4-phenoxybenzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(OC=4C=CC=CC=4)=CC=3)=CC=C2OC=1N(C)CC1CCN(C)C1 KYEKIAUYGKMCOK-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 208000011906 peptic ulcer disease Diseases 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 208000017497 prostate disease Diseases 0.000 claims 1
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
- 210000002345 respiratory system Anatomy 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 230000036269 ulceration Effects 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63711604P | 2004-12-17 | 2004-12-17 | |
| US60/637,116 | 2004-12-17 | ||
| PCT/US2005/045864 WO2006066173A2 (en) | 2004-12-17 | 2005-12-16 | Novel mch receptor antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008524249A JP2008524249A (ja) | 2008-07-10 |
| JP2008524249A5 true JP2008524249A5 (enExample) | 2009-02-12 |
| JP4988591B2 JP4988591B2 (ja) | 2012-08-01 |
Family
ID=36481254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007546990A Expired - Fee Related JP4988591B2 (ja) | 2004-12-17 | 2005-12-16 | 新規なｍｃｈ受容体アンタゴニスト |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7838543B2 (enExample) |
| EP (1) | EP1828177B1 (enExample) |
| JP (1) | JP4988591B2 (enExample) |
| CN (1) | CN101072775A (enExample) |
| AT (1) | ATE404555T1 (enExample) |
| AU (1) | AU2005316313B2 (enExample) |
| BR (1) | BRPI0517425A (enExample) |
| CA (1) | CA2589678A1 (enExample) |
| DE (1) | DE602005009021D1 (enExample) |
| DK (1) | DK1828177T3 (enExample) |
| ES (1) | ES2312048T3 (enExample) |
| MX (1) | MX2007007226A (enExample) |
| PL (1) | PL1828177T3 (enExample) |
| PT (1) | PT1828177E (enExample) |
| SI (1) | SI1828177T1 (enExample) |
| WO (1) | WO2006066173A2 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2005290436A1 (en) | 2004-10-01 | 2006-04-13 | Banyu Pharmaceutical Co.,Ltd | 2-arylcarboxamide-nitrogeneous heterocycle compound |
| CA2589695A1 (en) * | 2004-12-17 | 2006-06-22 | Eli Lilly And Company | Thiazolopyridinone derivates as mch receptor antagonists |
| AU2006208045B2 (en) | 2005-01-25 | 2012-08-30 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| US8153813B2 (en) * | 2007-12-20 | 2012-04-10 | Abbott Laboratories | Benzothiazole and benzooxazole derivatives and methods of use |
| CA2725481A1 (en) | 2008-06-18 | 2009-12-23 | Pfizer Limited | Nicotinamide derivatives |
| WO2010010435A2 (en) * | 2008-07-22 | 2010-01-28 | Glenmark Pharmaceutical S.A. | Fused oxazole and thiazole derivatives as trpms modulators |
| SA110310332B1 (ar) | 2009-05-01 | 2013-12-10 | Astrazeneca Ab | مركبات ميثانون (3 استبدال -ازيتيدين -1-يل )(5- فينيل -1، 3، 4- أوكساديازول -2-يل ) |
| AU2011275547B2 (en) | 2010-07-06 | 2015-10-29 | Astrazeneca Ab | Therapeutic agents 976 |
| ES2603032T3 (es) * | 2010-07-15 | 2017-02-23 | Bayer Intellectual Property Gmbh | Compuestos de 3-piridil-heteroarilcarboxamida como pesticidas |
| WO2012081563A1 (ja) * | 2010-12-14 | 2012-06-21 | 塩野義製薬株式会社 | 血管内皮リパーゼ阻害活性を有するベンゾチアゾールおよびアザベンゾチアゾール誘導体 |
| UY34194A (es) | 2011-07-15 | 2013-02-28 | Astrazeneca Ab | ?(3-(4-(espiroheterocíclico)metil)fenoxi)azetidin-1-il)(5-(fenil)-1,3,4-oxadiazol-2-il)metanona en el tratamiento de la obesidad? |
| JO3225B1 (ar) * | 2012-11-27 | 2018-03-08 | Lilly Co Eli | 6-((s)-1-{1-[5-(2-هيدروكسي-إيثوكسي)-بيريدين-2-يل]-1h-بيرازول-3-يل}إيثيل)-3h-1 ، 3-بنزو ثيازول-2- أون باعتباره مضاد مستقبل ampa يعتمد على tarp- جاما 8 |
| US9732095B2 (en) | 2014-01-13 | 2017-08-15 | Aurigene Discovery Technologies Limited | Bicyclic heterocyclyl derivatives as IRAK4 inhibitors |
| JP6802194B2 (ja) | 2015-06-22 | 2020-12-16 | アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | Ｎａｄｐｈオキシダーゼ４阻害剤 |
| AU2016293446A1 (en) * | 2015-07-15 | 2018-02-15 | Aurigene Discovery Technologies Limited | Substituted aza compounds as IRAK-4 inhibitors |
| CN110691589A (zh) | 2017-03-31 | 2020-01-14 | 奥列基因发现技术有限公司 | 用于治疗血液病的化合物和组合物 |
| FI3704108T3 (fi) | 2017-10-31 | 2024-05-23 | Curis Inc | Irak4-estäjä yhdistelmässä bcl-2-estäjän kanssa käytettäväksi syövän hoitoon |
| CN109485620A (zh) * | 2018-12-26 | 2019-03-19 | 安徽工大化工科技有限公司 | 一种2-甲氧基-6-甲氧基苯并噻唑的制备方法 |
| CN114008025A (zh) * | 2019-05-14 | 2022-02-01 | 美特波米德有限公司 | Acss2抑制剂和其使用方法 |
| IL307465A (en) | 2021-04-08 | 2023-12-01 | Curis Inc | Combined therapies for cancer treatment |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2565595A (en) | 1994-05-28 | 1995-12-21 | Smithkline Beecham Plc | Amide derivatives having 5ht1d-antagonist activity |
| PT971878E (pt) | 1997-02-27 | 2008-07-08 | Takeda Pharmaceutical | Compostos de amina, sua produção e utilização como inibidores da produção de amilóide beta |
| US7115750B1 (en) | 1999-09-20 | 2006-10-03 | Takeda Pharmaceutical Company Limited | Melanin concentrating hormone antagonist |
| US7091227B2 (en) * | 2000-02-07 | 2006-08-15 | Abbott Gmbh & Co. Kg | Benzothiazole derivatives |
| US6930185B2 (en) * | 2000-04-28 | 2005-08-16 | Takeda Chemical Industries, Ltd. | Melanin-concentrating hormone antagonist |
| US7229986B2 (en) * | 2000-05-16 | 2007-06-12 | Takeda Pharmaceutical Company Ltd. | Melanin-concentrating hormone antagonist |
| US6642252B2 (en) * | 2000-11-07 | 2003-11-04 | Bristol-Myers Squibb Company | Acid derivatives useful as serine protease inhibitors |
| DE10139126A1 (de) * | 2001-08-09 | 2003-02-20 | Ciba Sc Pfersee Gmbh | Zusammensetzungen aus Polysiloxanen, Fluorpolymeren und Extendern |
| DE10139416A1 (de) * | 2001-08-17 | 2003-03-06 | Aventis Pharma Gmbh | Aminoalkyl substituierte aromatische Bicyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| EP1463714A4 (en) * | 2001-12-10 | 2005-10-19 | Amgen Inc | VANILLOID RECEPTOR LIGANDS AND THEIR USE IN TREATMENTS |
| DE60329513D1 (de) * | 2002-07-30 | 2009-11-12 | Banyu Pharma Co Ltd | Antagonist des melanin-concentrating-hormone-rezeptors, enthaltend ein benzimidazolderivat als wirkstoff |
| EP1585726A1 (en) * | 2003-01-06 | 2005-10-19 | Eli Lilly And Company | Fused heterocyclic derivatives as ppar modulators |
| BRPI0608245A2 (pt) * | 2005-03-09 | 2009-12-01 | Hoffmann La Roche | compostos; processo para a sua fabricação; composições farmacêuticas; método para o tratamento e/ou prevenção de doenças que estejam associadas à modulação de receptores de sst subtipo 5 e uso dos compostos |
-
2005
- 2005-12-16 CA CA002589678A patent/CA2589678A1/en not_active Abandoned
- 2005-12-16 PT PT05854552T patent/PT1828177E/pt unknown
- 2005-12-16 DE DE602005009021T patent/DE602005009021D1/de active Active
- 2005-12-16 DK DK05854552T patent/DK1828177T3/da active
- 2005-12-16 AU AU2005316313A patent/AU2005316313B2/en not_active Ceased
- 2005-12-16 SI SI200530456T patent/SI1828177T1/sl unknown
- 2005-12-16 PL PL05854552T patent/PL1828177T3/pl unknown
- 2005-12-16 US US11/719,576 patent/US7838543B2/en not_active Expired - Fee Related
- 2005-12-16 BR BRPI0517425-2A patent/BRPI0517425A/pt not_active IP Right Cessation
- 2005-12-16 CN CNA2005800418488A patent/CN101072775A/zh active Pending
- 2005-12-16 MX MX2007007226A patent/MX2007007226A/es active IP Right Grant
- 2005-12-16 EP EP05854552A patent/EP1828177B1/en not_active Expired - Lifetime
- 2005-12-16 ES ES05854552T patent/ES2312048T3/es not_active Expired - Lifetime
- 2005-12-16 AT AT05854552T patent/ATE404555T1/de active
- 2005-12-16 WO PCT/US2005/045864 patent/WO2006066173A2/en not_active Ceased
- 2005-12-16 JP JP2007546990A patent/JP4988591B2/ja not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2008524249A5 (enExample) | ||
| ES2605388T3 (es) | Compuesto inhibidor de Trk | |
| JP5954510B1 (ja) | Ｔｒｋ阻害化合物 | |
| JP6117430B2 (ja) | 選択的ヒストン脱アセチル化酵素抑制剤としての新規化合物およびこれを含む薬剤学的組成物 | |
| RU2008100606A (ru) | Ингибиторы сфингозинкиназы | |
| RU2006138433A (ru) | Сульфонамидтиазолпиридиновые производные как активаторы глюкокиназы, пригодные для лечения диабета типа 2 | |
| JP2008524250A5 (enExample) | ||
| ES2396741T3 (es) | Nuevo derivado de pirrol que tiene un grupo ureído y un grupo aminocarbonilo como sustituyentes | |
| JP2006509801A5 (enExample) | ||
| TW200403223A (en) | Novel compounds | |
| CA2672373A1 (en) | Nicotinamide derivatives as inhibitors of h-pgds and their use for treating prostaglandin d2 mediated diseases | |
| RU2007105970A (ru) | Пиперидиновые производные в качестве лигандов гистаминового из рецептора | |
| RU2009148673A (ru) | Производные пиразинона и их применение для лечения легочных заболеваний | |
| TW200404796A (en) | Nitrogen-containing compound | |
| CN112204023A (zh) | 因子XIIa抑制剂 | |
| CA2473892A1 (en) | Novel quinoline derivatives | |
| JP2022553351A (ja) | Ｅｒｋ１およびｅｒｋ２の複素環式阻害剤の使用のための改善された方法、キット、組成物、ならびに投与レジメン | |
| NZ546012A (en) | Bicyclic [3.1.0] derivatives as glycine transporter inhibitors | |
| ES2441176T3 (es) | Nuevo compuesto que tiene un grupo 4-piridilalquiltio como sustituyente | |
| JP2014521618A (ja) | 置換複素環アザ誘導体 | |
| RU2005137706A (ru) | Производное [1, 2, 4] триазоло [1, 5-а] пиримидин -2-илмочевины и его применение | |
| CA2615611A1 (en) | Indazole derivatives | |
| CA2373395A1 (en) | Sulfonyl pyridazinone compounds useful as aldose reductase inhibitors | |
| JP5815874B2 (ja) | Ｈｄｌコレステロール上昇剤としての３−ピリジンカルボン酸ヒドラジド | |
| CA2557789A1 (en) | Pyrazolyl indolyl derivatives as ppar activators |