JP2008524249A5 - - Google Patents
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- 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
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- 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
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| WO2006066174A1 (en) * | 2004-12-17 | 2006-06-22 | Eli Lilly And Company | Thiazolopyridinone derivates as mch receptor antagonists |
| PL1848435T3 (pl) | 2005-01-25 | 2016-08-31 | Synta Pharmaceuticals Corp | Związki przeciwko zapaleniom i zastosowania związane z odpornością |
| 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 |
| JP5996532B2 (ja) * | 2010-07-15 | 2016-09-21 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 有害生物防除剤としての新規複素環式化合物 |
| TW201305152A (zh) * | 2010-12-14 | 2013-02-01 | Shionogi & Co | 具有血管內皮脂肪酶抑制活性之苯并噻唑及吖苯并噻唑衍生物 |
| 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 |
| LT3466955T (lt) | 2014-01-13 | 2021-02-25 | Aurigene Discovery Technologies Limited | Oksazol[4,5-b]piridino ir tiazol[4,5-b]piridino darinių, kaip irak4 inhibitorių, skirtų vėžio gydymui, gamybos būdas |
| 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 |
| CN108024971A (zh) * | 2015-07-15 | 2018-05-11 | 奥列基因发现技术有限公司 | 作为irak-4抑制剂的取代的氮杂化合物 |
| EP3600270B1 (en) * | 2017-03-31 | 2023-06-14 | Aurigene Oncology Limited | Compounds and compositions for treating hematological disorders |
| HUE067356T2 (hu) | 2017-10-31 | 2024-10-28 | Curis Inc | IRAK4 inhibitor és BCL-2 inhibitor kombinációban, rák kezelésére való felhasználásra |
| 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 |
| JP2022532718A (ja) * | 2019-05-14 | 2022-07-19 | メタボメッド リミテッド | Ａｃｓｓ２阻害剤およびその使用方法 |
| EP4319750A4 (en) | 2021-04-08 | 2025-02-26 | Curis, Inc. | COMBINATION THERAPIES FOR THE TREATMENT OF CANCER |
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 |
| ES2300119T3 (es) | 1997-02-27 | 2008-06-01 | Takeda Pharmaceutical Company Limited | Compuestos de amina, su produccion y su uso como inhibidores de la produccion de beta-amiloide. |
| EP1218336A2 (en) | 1999-09-20 | 2002-07-03 | Takeda Chemical Industries, Ltd. | Melanin concentrating hormone antagonist |
| KR20020084116A (ko) | 2000-02-07 | 2002-11-04 | 애보트 게엠베하 운트 콤파니 카게 | 2-벤조티아졸릴 우레아 유도체 및 이의 단백질 키나제억제제로서의 용도 |
| EP1285651B1 (en) * | 2000-04-28 | 2010-09-01 | Takeda Pharmaceutical Company Limited | Melanin concentrating hormone antagonists |
| US7229986B2 (en) * | 2000-05-16 | 2007-06-12 | Takeda Pharmaceutical Company Ltd. | Melanin-concentrating hormone antagonist |
| EP1332131A2 (en) * | 2000-11-07 | 2003-08-06 | 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 |
| JP2005518371A (ja) * | 2001-12-10 | 2005-06-23 | アムジエン・インコーポレーテツド | バニロイド受容体リガンド及び治療に於けるこれらの使用 |
| JP4595542B2 (ja) * | 2002-07-30 | 2010-12-08 | 萬有製薬株式会社 | ベンズイミダゾール誘導体を有効成分とするメラニン凝集ホルモン受容体拮抗剤 |
| AU2003296405A1 (en) | 2003-01-06 | 2004-08-10 | Eli Lilly And Company | Fused heterocyclic derivatives as ppar modulators |
| WO2006094682A1 (en) * | 2005-03-09 | 2006-09-14 | F. Hoffmann-La Roche Ag | Benzothiazole, thiazolopyridine, benzooxazole and oxazolopyridine derivatives as antidiabetic compounds |
-
2005
- 2005-12-16 DE DE602005009021T patent/DE602005009021D1/de not_active Expired - Lifetime
- 2005-12-16 WO PCT/US2005/045864 patent/WO2006066173A2/en not_active Ceased
- 2005-12-16 EP EP05854552A patent/EP1828177B1/en not_active Expired - Lifetime
- 2005-12-16 US US11/719,576 patent/US7838543B2/en not_active Expired - Fee Related
- 2005-12-16 MX MX2007007226A patent/MX2007007226A/es active IP Right Grant
- 2005-12-16 JP JP2007546990A patent/JP4988591B2/ja not_active Expired - Fee Related
- 2005-12-16 AU AU2005316313A patent/AU2005316313B2/en not_active Ceased
- 2005-12-16 CN CNA2005800418488A patent/CN101072775A/zh active Pending
- 2005-12-16 AT AT05854552T patent/ATE404555T1/de active
- 2005-12-16 BR BRPI0517425-2A patent/BRPI0517425A/pt not_active IP Right Cessation
- 2005-12-16 PT PT05854552T patent/PT1828177E/pt unknown
- 2005-12-16 ES ES05854552T patent/ES2312048T3/es not_active Expired - Lifetime
- 2005-12-16 SI SI200530456T patent/SI1828177T1/sl unknown
- 2005-12-16 DK DK05854552T patent/DK1828177T3/da active
- 2005-12-16 PL PL05854552T patent/PL1828177T3/pl unknown
- 2005-12-16 CA CA002589678A patent/CA2589678A1/en not_active Abandoned
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