JP2007516173A5 - - Google Patents
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- Publication number
- JP2007516173A5 JP2007516173A5 JP2006517466A JP2006517466A JP2007516173A5 JP 2007516173 A5 JP2007516173 A5 JP 2007516173A5 JP 2006517466 A JP2006517466 A JP 2006517466A JP 2006517466 A JP2006517466 A JP 2006517466A JP 2007516173 A5 JP2007516173 A5 JP 2007516173A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- indazol
- oxo
- tetrahydro
- pyrimidinecarboxamide
- 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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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 10
- 239000012453 solvate Substances 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 8
- -1 methoxy, ethoxy Chemical group 0.000 claims 8
- WOOLOAFADUQHNQ-UHFFFAOYSA-N 4-(3,5-difluorophenyl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxylic acid Chemical compound N1C(=O)NC(C)=C(C(O)=O)C1C1=CC(F)=CC(F)=C1 WOOLOAFADUQHNQ-UHFFFAOYSA-N 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- MODPFIYPSWMRNZ-UHFFFAOYSA-N 3-ethyl-6-(4-fluorophenyl)-n-(1h-indazol-5-yl)-4-methyl-2-oxo-1,6-dihydropyrimidine-5-carboxamide Chemical compound C=1C=C2NN=CC2=CC=1NC(=O)C1=C(C)N(CC)C(=O)NC1C1=CC=C(F)C=C1 MODPFIYPSWMRNZ-UHFFFAOYSA-N 0.000 claims 2
- VRJZWJDDURABEQ-UHFFFAOYSA-N 4-[4-[4-(dimethylamino)phenyl]phenyl]-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C1=CC=C(C2C(=C(C)NC(=O)N2)C(=O)NC=2C=C3C=NNC3=CC=2)C=C1 VRJZWJDDURABEQ-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
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 229940095102 methyl benzoate Drugs 0.000 claims 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- ZRZGFGPKMTUBOI-UHFFFAOYSA-N 2-amino-4-(4-fluorophenyl)-n-(1h-indazol-5-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxamide Chemical compound N1=C(N)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=C(F)C=C1 ZRZGFGPKMTUBOI-UHFFFAOYSA-N 0.000 claims 1
- WYHCBMHBRCUTRB-UHFFFAOYSA-N 3-[5-(1h-indazol-5-ylcarbamoyl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidin-4-yl]benzoic acid Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=CC(C(O)=O)=C1 WYHCBMHBRCUTRB-UHFFFAOYSA-N 0.000 claims 1
- IAJLFGXHHNOMDW-UHFFFAOYSA-N 3-benzyl-6-(4-fluorophenyl)-n-(1h-indazol-5-yl)-4-methyl-2-oxo-1,6-dihydropyrimidine-5-carboxamide Chemical compound CC1=C(C(=O)NC=2C=C3C=NNC3=CC=2)C(C=2C=CC(F)=CC=2)NC(=O)N1CC1=CC=CC=C1 IAJLFGXHHNOMDW-UHFFFAOYSA-N 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- UWRAYOBUXZXUKE-UHFFFAOYSA-N 4-(1,3-benzodioxol-4-yl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=C2NN=CC2=CC(NC(=O)C2=C(NC(=O)NC2C=2C=3OCOC=3C=CC=2)C)=C1 UWRAYOBUXZXUKE-UHFFFAOYSA-N 0.000 claims 1
- HOCWQVUNZAUIQW-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=C2NN=CC2=CC(NC(=O)C2=C(NC(=O)NC2C=2C=C3OCOC3=CC=2)C)=C1 HOCWQVUNZAUIQW-UHFFFAOYSA-N 0.000 claims 1
- KDUCIBONFZVABB-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=C2NN=CC2=CC(NC(=O)C2=C(NC(=O)NC2C=2SC3=CC=CC=C3N=2)C)=C1 KDUCIBONFZVABB-UHFFFAOYSA-N 0.000 claims 1
- GUHNKNQAOXTXQN-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=C2NN=CC2=CC(NC(=O)C2=C(NC(=O)NC2C=2OC3=CC=CC=C3C=2)C)=C1 GUHNKNQAOXTXQN-UHFFFAOYSA-N 0.000 claims 1
- SMMDAUKFRAJTRK-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=C2NN=CC2=CC(NC(=O)C2=C(NC(=O)NC2C=2SC3=CC=CC=C3C=2)C)=C1 SMMDAUKFRAJTRK-UHFFFAOYSA-N 0.000 claims 1
- GSTIZTSTBSSNCC-UHFFFAOYSA-N 4-(2,2-diphenylethenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 GSTIZTSTBSSNCC-UHFFFAOYSA-N 0.000 claims 1
- BXGNHZZBUKULEU-UHFFFAOYSA-N 4-(2,3-dihydro-1,4-benzodioxin-6-yl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=C2NN=CC2=CC(NC(=O)C2=C(NC(=O)NC2C=2C=C3OCCOC3=CC=2)C)=C1 BXGNHZZBUKULEU-UHFFFAOYSA-N 0.000 claims 1
- DTHHVWPUGFFNNW-UHFFFAOYSA-N 4-(2,4-difluorophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=C(F)C=C1F DTHHVWPUGFFNNW-UHFFFAOYSA-N 0.000 claims 1
- OHTUZZOCMWKINM-UHFFFAOYSA-N 4-(2,6-difluorophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=C(F)C=CC=C1F OHTUZZOCMWKINM-UHFFFAOYSA-N 0.000 claims 1
- AVEDGCCFEOGVGA-UHFFFAOYSA-N 4-(2-chlorophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=CC=C1Cl AVEDGCCFEOGVGA-UHFFFAOYSA-N 0.000 claims 1
- NONJJUKJZZGMCM-UHFFFAOYSA-N 4-(2-chloroquinolin-3-yl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=C2NN=CC2=CC(NC(=O)C2=C(NC(=O)NC2C=2C(=NC3=CC=CC=C3C=2)Cl)C)=C1 NONJJUKJZZGMCM-UHFFFAOYSA-N 0.000 claims 1
- VVDLARFFZQVDKD-UHFFFAOYSA-N 4-(2-fluorophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=CC=C1F VVDLARFFZQVDKD-UHFFFAOYSA-N 0.000 claims 1
- RUUNIOMLHMGMAM-UHFFFAOYSA-N 4-(2-hydroxy-4-methoxyphenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound OC1=CC(OC)=CC=C1C1C(C(=O)NC=2C=C3C=NNC3=CC=2)=C(C)NC(=O)N1 RUUNIOMLHMGMAM-UHFFFAOYSA-N 0.000 claims 1
- SECAFBMQKJTYFP-UHFFFAOYSA-N 4-(2h-chromen-3-yl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=C2NN=CC2=CC(NC(=O)C2=C(NC(=O)NC2C=2COC3=CC=CC=C3C=2)C)=C1 SECAFBMQKJTYFP-UHFFFAOYSA-N 0.000 claims 1
- ILZDPPZKFLERTA-UHFFFAOYSA-N 4-(3,4-diethoxyphenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=C(OCC)C(OCC)=CC=C1C1C(C(=O)NC=2C=C3C=NNC3=CC=2)=C(C)NC(=O)N1 ILZDPPZKFLERTA-UHFFFAOYSA-N 0.000 claims 1
- BYHLVBRHNYDQMW-UHFFFAOYSA-N 4-(3,4-difluorophenyl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxylic acid Chemical compound N1C(=O)NC(C)=C(C(O)=O)C1C1=CC=C(F)C(F)=C1 BYHLVBRHNYDQMW-UHFFFAOYSA-N 0.000 claims 1
- UXUBQCRXPASGDL-UHFFFAOYSA-N 4-(3,4-difluorophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=C(F)C(F)=C1 UXUBQCRXPASGDL-UHFFFAOYSA-N 0.000 claims 1
- YFNRWWHQAZMLEB-UHFFFAOYSA-N 4-(3,4-difluorophenyl)-n-[3-(4-fluoroanilino)-1h-indazol-5-yl]-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C(NC=4C=CC(F)=CC=4)=NNC3=CC=2)C1C1=CC=C(F)C(F)=C1 YFNRWWHQAZMLEB-UHFFFAOYSA-N 0.000 claims 1
- CKVSZZUYZWKVSF-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1C(C(=O)NC=2C=C3C=NNC3=CC=2)=C(C)NC(=O)N1 CKVSZZUYZWKVSF-UHFFFAOYSA-N 0.000 claims 1
- QYJPBLIDLPMOLY-UHFFFAOYSA-N 4-(3,5-dibromophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC(Br)=CC(Br)=C1 QYJPBLIDLPMOLY-UHFFFAOYSA-N 0.000 claims 1
- YOOJIJWZLORODW-UHFFFAOYSA-N 4-(3-aminophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=CC(N)=C1 YOOJIJWZLORODW-UHFFFAOYSA-N 0.000 claims 1
- NBKFDQQXRCAJKL-UHFFFAOYSA-N 4-(3-bromo-4-fluorophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=C(F)C(Br)=C1 NBKFDQQXRCAJKL-UHFFFAOYSA-N 0.000 claims 1
- DNOFJVRWWPPNDJ-UHFFFAOYSA-N 4-(3-bromophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=CC(Br)=C1 DNOFJVRWWPPNDJ-UHFFFAOYSA-N 0.000 claims 1
- FKAYINDOJIDVDH-UHFFFAOYSA-N 4-(3-chloro-4-fluorophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=C(F)C(Cl)=C1 FKAYINDOJIDVDH-UHFFFAOYSA-N 0.000 claims 1
- QJFHBSOYEIWXDM-UHFFFAOYSA-N 4-(3-chlorophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=CC(Cl)=C1 QJFHBSOYEIWXDM-UHFFFAOYSA-N 0.000 claims 1
- OOALCMJXEHJHLS-UHFFFAOYSA-N 4-(3-cyano-4-fluorophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=C(F)C(C#N)=C1 OOALCMJXEHJHLS-UHFFFAOYSA-N 0.000 claims 1
- KSJVKIPUWJHQNL-UHFFFAOYSA-N 4-(3-cyanophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=CC(C#N)=C1 KSJVKIPUWJHQNL-UHFFFAOYSA-N 0.000 claims 1
- IYUJOEHDRMLQGE-UHFFFAOYSA-N 4-(3-fluoro-4-methoxyphenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1C1C(C(=O)NC=2C=C3C=NNC3=CC=2)=C(C)NC(=O)N1 IYUJOEHDRMLQGE-UHFFFAOYSA-N 0.000 claims 1
- JFQBMZRXDXNOQW-UHFFFAOYSA-N 4-(3-hydroxy-4-methoxyphenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=C(O)C(OC)=CC=C1C1C(C(=O)NC=2C=C3C=NNC3=CC=2)=C(C)NC(=O)N1 JFQBMZRXDXNOQW-UHFFFAOYSA-N 0.000 claims 1
- AXRZRKVKXZAULO-UHFFFAOYSA-N 4-(3-hydroxyphenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=CC(O)=C1 AXRZRKVKXZAULO-UHFFFAOYSA-N 0.000 claims 1
- WAZSZNQPAUATDJ-UHFFFAOYSA-N 4-(3-imidazol-1-ylphenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C(C=1)=CC=CC=1N1C=CN=C1 WAZSZNQPAUATDJ-UHFFFAOYSA-N 0.000 claims 1
- AAMHSIWFDKXUMZ-UHFFFAOYSA-N 4-(4-acetamidophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1C(C(=O)NC=2C=C3C=NNC3=CC=2)=C(C)NC(=O)N1 AAMHSIWFDKXUMZ-UHFFFAOYSA-N 0.000 claims 1
- CBEOKSFOIUBPOJ-UHFFFAOYSA-N 4-(4-bromophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=C(Br)C=C1 CBEOKSFOIUBPOJ-UHFFFAOYSA-N 0.000 claims 1
- NCPQBDQHXISGFZ-UHFFFAOYSA-N 4-(4-carbamoylphenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=C(C(N)=O)C=C1 NCPQBDQHXISGFZ-UHFFFAOYSA-N 0.000 claims 1
- YJJMMMPXUUTXQO-UHFFFAOYSA-N 4-(4-chloro-2-fluorophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=C(Cl)C=C1F YJJMMMPXUUTXQO-UHFFFAOYSA-N 0.000 claims 1
- HHUBHLZUJCZEHF-UHFFFAOYSA-N 4-(4-chloro-2-fluorophenyl)-n-[3-(3,5-difluoroanilino)-1h-indazol-5-yl]-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C(NC=4C=C(F)C=C(F)C=4)=NNC3=CC=2)C1C1=CC=C(Cl)C=C1F HHUBHLZUJCZEHF-UHFFFAOYSA-N 0.000 claims 1
- LFFLRGYZVKOWTR-UHFFFAOYSA-N 4-(4-chlorophenyl)-6-(1h-indazol-5-yl)-1,3,4,7-tetrahydropyrrolo[3,4-d]pyrimidine-2,5-dione Chemical compound C1=CC(Cl)=CC=C1C1C(C(=O)N(C2)C=3C=C4C=NNC4=CC=3)=C2NC(=O)N1 LFFLRGYZVKOWTR-UHFFFAOYSA-N 0.000 claims 1
- JJQGYFOALOWJOT-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=C(Cl)C=C1 JJQGYFOALOWJOT-UHFFFAOYSA-N 0.000 claims 1
- ZSMLVUOYSUEJMJ-UHFFFAOYSA-N 4-(4-cyanophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=C(C#N)C=C1 ZSMLVUOYSUEJMJ-UHFFFAOYSA-N 0.000 claims 1
- UAJZJYHSCDDVGF-UHFFFAOYSA-N 4-(4-fluoro-3-nitrophenyl)-n-(1h-indazol-5-yl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C1=CC=C(F)C([N+]([O-])=O)=C1 UAJZJYHSCDDVGF-UHFFFAOYSA-N 0.000 claims 1
- RNZYWDUEQHKAKP-UHFFFAOYSA-N 4-(4-fluorophenyl)-6-(1h-indazol-5-yl)-1,3,4,4a,7,7a-hexahydropyrrolo[3,4-d]pyrimidine-2,5-dione Chemical compound C1=CC(F)=CC=C1C1C2C(=O)N(C=3C=C4C=NNC4=CC=3)CC2NC(=O)N1 RNZYWDUEQHKAKP-UHFFFAOYSA-N 0.000 claims 1
- BMSWNBUEXKCYMK-UHFFFAOYSA-N 4-(4-fluorophenyl)-6-(furan-2-yl)-n-(1h-indazol-5-yl)-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=CC(F)=CC=C1C1C(C(=O)NC=2C=C3C=NNC3=CC=2)=C(C=2OC=CC=2)NC(=O)N1 BMSWNBUEXKCYMK-UHFFFAOYSA-N 0.000 claims 1
- LEAYPJKAZZLJQP-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-(1h-indazol-5-yl)-1,3,6-trimethyl-2-oxo-4h-pyrimidine-5-carboxamide Chemical compound C=1C=C2NN=CC2=CC=1NC(=O)C1=C(C)N(C)C(=O)N(C)C1C1=CC=C(F)C=C1 LEAYPJKAZZLJQP-UHFFFAOYSA-N 0.000 claims 1
- SKVWNRQWUBCWGF-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-(1h-indazol-5-yl)-2,6-dimethyl-1,4-dihydropyrimidine-5-carboxamide Chemical compound C=1C=C2NN=CC2=CC=1NC(=O)C1=C(C)NC(C)=NC1C1=CC=C(F)C=C1 SKVWNRQWUBCWGF-UHFFFAOYSA-N 0.000 claims 1
- KYZSREXWIWGHAA-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-(1h-indazol-5-yl)-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=CC(F)=CC=C1C1C(C(=O)NC=2C=C3C=NNC3=CC=2)=CNC(=O)N1 KYZSREXWIWGHAA-UHFFFAOYSA-N 0.000 claims 1
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- IZGMQRPDTGROBW-UHFFFAOYSA-N n-(1h-indazol-5-yl)-6-methyl-4-[5-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]thiophen-2-yl]-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=CC=2)C1C(S1)=CC=C1C=1C=C(C(F)(F)F)N(C)N=1 IZGMQRPDTGROBW-UHFFFAOYSA-N 0.000 claims 1
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- BGWIWNHRYSHQDX-UHFFFAOYSA-N n-(1h-indazol-5-yl)-6-methyl-4-naphthalen-2-yl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=C2NN=CC2=CC(NC(=O)C2=C(NC(=O)NC2C=2C=C3C=CC=CC3=CC=2)C)=C1 BGWIWNHRYSHQDX-UHFFFAOYSA-N 0.000 claims 1
- QILDKOUKJADHOQ-UHFFFAOYSA-N n-(1h-indazol-5-yl)-6-methyl-4-naphthalen-2-yl-2-sulfanylidene-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=C2NN=CC2=CC(NC(=O)C2=C(NC(=S)NC2C=2C=C3C=CC=CC3=CC=2)C)=C1 QILDKOUKJADHOQ-UHFFFAOYSA-N 0.000 claims 1
- HUGYPGOVMNNWNK-UHFFFAOYSA-N n-(3-bromo-2h-indazol-5-yl)-4-(4-fluorophenyl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C(Br)=NNC3=CC=2)C1C1=CC=C(F)C=C1 HUGYPGOVMNNWNK-UHFFFAOYSA-N 0.000 claims 1
- LGOTWMHIQPNRNZ-UHFFFAOYSA-N n-(3-bromo-2h-indazol-5-yl)-6-methyl-2-oxo-4-thiophen-3-yl-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C(Br)=NNC3=CC=2)C1C=1C=CSC=1 LGOTWMHIQPNRNZ-UHFFFAOYSA-N 0.000 claims 1
- WXHZPKMSRXQOAG-UHFFFAOYSA-N n-(3-bromo-2h-indazol-5-yl)-6-methyl-4-naphthalen-2-yl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=C2NN=C(Br)C2=CC(NC(=O)C2=C(NC(=O)NC2C=2C=C3C=CC=CC3=CC=2)C)=C1 WXHZPKMSRXQOAG-UHFFFAOYSA-N 0.000 claims 1
- TUBXQMQXGWKLFD-UHFFFAOYSA-N n-(3-chloro-2h-indazol-5-yl)-4-(4-fluorophenyl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C(Cl)=NNC3=CC=2)C1C1=CC=C(F)C=C1 TUBXQMQXGWKLFD-UHFFFAOYSA-N 0.000 claims 1
- RDRNINVCHIGQHQ-UHFFFAOYSA-N n-(3-chloro-2h-indazol-5-yl)-6-methyl-4-naphthalen-2-yl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C1=C2NN=C(Cl)C2=CC(NC(=O)C2=C(NC(=O)NC2C=2C=C3C=CC=CC3=CC=2)C)=C1 RDRNINVCHIGQHQ-UHFFFAOYSA-N 0.000 claims 1
- NYMKLMOPVIINFF-UHFFFAOYSA-N n-(6-chloro-1h-indazol-5-yl)-6-methyl-4-naphthalen-2-yl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound C=1C=C2C=CC=CC2=CC=1C1NC(=O)NC(C)=C1C(=O)NC(C(=C1)Cl)=CC2=C1NN=C2 NYMKLMOPVIINFF-UHFFFAOYSA-N 0.000 claims 1
- UTCUKMMHEWXRIV-UHFFFAOYSA-N n-(6-fluoro-1h-indazol-5-yl)-4-(4-fluorophenyl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C(=CC=3NN=CC=3C=2)F)C1C1=CC=C(F)C=C1 UTCUKMMHEWXRIV-UHFFFAOYSA-N 0.000 claims 1
- FFJHNKDMDJAMRA-UHFFFAOYSA-N n-(7-chloro-1h-indazol-5-yl)-4-(4-fluorophenyl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C=NNC3=C(Cl)C=2)C1C1=CC=C(F)C=C1 FFJHNKDMDJAMRA-UHFFFAOYSA-N 0.000 claims 1
- LRNPBXHHMDJOIP-UHFFFAOYSA-N n-(7-chloro-1h-indazol-5-yl)-6-methyl-4-naphthalen-2-yl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound ClC1=C2NN=CC2=CC(NC(=O)C2=C(NC(=O)NC2C=2C=C3C=CC=CC3=CC=2)C)=C1 LRNPBXHHMDJOIP-UHFFFAOYSA-N 0.000 claims 1
- ZOTFTFUKLXZTLO-UHFFFAOYSA-N n-[3-(3,5-difluoroanilino)-1h-indazol-5-yl]-4-(3,4-difluorophenyl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C(NC=4C=C(F)C=C(F)C=4)=NNC3=CC=2)C1C1=CC=C(F)C(F)=C1 ZOTFTFUKLXZTLO-UHFFFAOYSA-N 0.000 claims 1
- RJKCBUGBEJUQIV-UHFFFAOYSA-N n-[3-(3,5-difluoroanilino)-1h-indazol-5-yl]-4-(3,5-difluorophenyl)-6-methyl-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C(NC=4C=C(F)C=C(F)C=4)=NNC3=CC=2)C1C1=CC(F)=CC(F)=C1 RJKCBUGBEJUQIV-UHFFFAOYSA-N 0.000 claims 1
- QBZFUFVYEVDYOT-UHFFFAOYSA-N n-[3-(3,5-difluoroanilino)-1h-indazol-5-yl]-6-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(C)=C(C(=O)NC=2C=C3C(NC=4C=C(F)C=C(F)C=4)=NNC3=CC=2)C1C1=CC=C(C(F)(F)F)C=C1 QBZFUFVYEVDYOT-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 0 *C(*)c1cc(cccc2)c2[s]1 Chemical compound *C(*)c1cc(cccc2)c2[s]1 0.000 description 4
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| US7592357B2 (en) * | 2004-02-20 | 2009-09-22 | Smithkline Beecham Corporation | Compounds |
| DE102004028862A1 (de) * | 2004-06-15 | 2005-12-29 | Merck Patent Gmbh | 3-Aminoindazole |
| WO2006009889A1 (en) * | 2004-06-17 | 2006-01-26 | Smithkline Beecham Corporation | Novel inhibitors of rho-kinases |
| WO2006074293A2 (en) * | 2005-01-07 | 2006-07-13 | President And Fellows Of Harvard College | Bicyclic dihydropyrimidines as eg5 inhibitors |
| US7820821B2 (en) * | 2006-02-10 | 2010-10-26 | Transtech Pharma, Inc. | Benzazole derivatives, compositions, and methods of use as aurora kinase inhibitors |
| WO2008061109A2 (en) * | 2006-11-15 | 2008-05-22 | Forest Laboratories Holdings Limited | Indazole derivatives useful as melanin concentrating receptor ligands |
| JP2010515744A (ja) | 2007-01-10 | 2010-05-13 | アルバニー モレキュラー リサーチ， インコーポレイテッド | ５−ピリジノン置換インダゾール |
| CN101861311A (zh) | 2007-07-21 | 2010-10-13 | 阿尔巴尼分子研究公司 | 5-吡啶酮取代的吲唑 |
| CA2768396A1 (en) * | 2009-07-30 | 2011-02-03 | F. Hoffmann-La Roche Ag | Dihydropyrimidone amides as p2x7 modulators |
| HRP20170736T1 (hr) * | 2010-05-07 | 2017-07-28 | Glaxosmithkline Llc | Indoli |
| ES2534804T3 (es) | 2010-05-07 | 2015-04-28 | Glaxosmithkline Llc | Indazoles |
| WO2012065067A2 (en) | 2010-11-12 | 2012-05-18 | Georgetown University | Immortalization of epithelial cells and methods of use |
| JO3438B1 (ar) | 2011-04-13 | 2019-10-20 | Epizyme Inc | مركبات بنزين مستبدلة بأريل أو أريل غير متجانس |
| US9174984B2 (en) | 2011-10-24 | 2015-11-03 | Glaxosmithkline Intellectual Property (No.2) Limited | Chemical compounds |
| EP2773754B1 (en) | 2011-11-04 | 2016-08-03 | Glaxosmithkline Intellectual Property (No. 2) Limited | Compounds for use in the treatment of T-cell mediated diseases |
| JP6250561B2 (ja) * | 2012-02-08 | 2017-12-20 | サノビオン ファーマシューティカルズ インクＳｕｎｏｖｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | ヘテロアリール化合物およびそれらの使用方法 |
| SG10201705989YA (en) | 2012-10-15 | 2017-08-30 | Epizyme Inc | Substituted benzene compounds |
| US9629851B2 (en) | 2013-09-20 | 2017-04-25 | Stitching Het Nederlands Kanker Institut—Antoni Van Leeuwenhoek Ziekenhuis | ROCK in combination with MAPK pathway |
| KR20170020527A (ko) | 2014-06-27 | 2017-02-22 | 더 리젠츠 오브 더 유니버시티 오브 캘리포니아 | 배양된 포유동물 윤부 줄기세포, 이를 생성하는 방법, 및 이의 용도 |
| WO2016023028A2 (en) * | 2014-08-08 | 2016-02-11 | The Regents Of The University Of Michigan | G protein-coupled receptor kinase 2 inhibitors and methods for use of the same |
| US10100285B2 (en) | 2015-04-03 | 2018-10-16 | Propagenix Inc. | Ex vivo proliferation of epithelial cells |
| DK3277799T3 (en) | 2015-04-03 | 2020-12-14 | Propagenix Inc | Ex vivo proliferation af epithelceller |
| EP3313396B1 (en) | 2015-06-26 | 2021-12-15 | The Regents of The University of Michigan | G protein-coupled receptor kinase inhibitors and methods for use of the same |
| EP3347450B1 (en) | 2015-09-11 | 2021-03-17 | Propagenix Inc. | Ex vivo proliferation of epithelial cells |
| EA201990399A1 (ru) | 2016-07-29 | 2019-07-31 | Суновион Фармасьютикалз, Инк. | Соединения, композиции и их применение |
| CN116514761A (zh) | 2016-07-29 | 2023-08-01 | 赛诺维信制药公司 | 化合物、组合物及其用途 |
| EP3654972A4 (en) * | 2017-07-21 | 2021-03-17 | Kadmon Corporation, LLC | KINASE PROTEIN INHIBITORS CONTAINING A COIL COIL ASSOCIATED WITH RHO |
| CN111183138A (zh) | 2017-08-02 | 2020-05-19 | 赛诺维信制药公司 | 异色满化合物以及用途 |
| US20210189351A1 (en) | 2018-08-20 | 2021-06-24 | Propagenix Inc. | Epithelial cell spheroids |
| WO2020047229A1 (en) | 2018-08-29 | 2020-03-05 | University Of Massachusetts | Inhibition of protein kinases to treat friedreich ataxia |
| UY38427A (es) | 2018-10-26 | 2020-05-29 | Novartis Ag | Métodos y composiciones para terapia con células oculares |
| JP7703449B2 (ja) | 2019-03-14 | 2025-07-07 | スミトモ・ファーマ・アメリカ・インコーポレイテッド | イソクロマニル化合物の塩およびその結晶体、ならびにそれらの製造方法、治療用途および医薬組成物 |
| US20230172929A1 (en) * | 2019-08-08 | 2023-06-08 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Novel peripheral cannabinoid-1 receptor antagonists |
| JP2023522784A (ja) | 2020-04-27 | 2023-05-31 | ノバルティス アーゲー | 眼細胞療法のための方法及び組成物 |
| US20240174637A1 (en) * | 2021-01-22 | 2024-05-30 | Grazia Piizzi | Degraders of grk2 and uses thereof |
| WO2023069949A1 (en) | 2021-10-18 | 2023-04-27 | Evia Life Sciences Inc. | Compositions and methods of use thereof for treating liver fibrosis |
| CA3235862A1 (en) | 2021-10-22 | 2023-04-27 | Takahiro Ochiya | Methods for making extracellular vesicles, and compositions and methods of use thereof |
Family Cites Families (6)
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| WO2001027105A1 (en) * | 1999-10-12 | 2001-04-19 | Takeda Chemical Industries, Ltd. | Pyrimidine-5-carboxamide compounds, process for producing the same and use thereof |
| CA2432799C (en) * | 2000-12-21 | 2008-08-19 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| WO2002066443A2 (en) * | 2001-02-21 | 2002-08-29 | Ono Pharmaceutical Co., Ltd. | 2-thioxo-1,2,3,4-tetrahydropyrimidine derivatives |
| ATE449763T1 (de) | 2001-04-16 | 2009-12-15 | Eisai R&D Man Co Ltd | 1h-indazolverbindungen die jnk hemmen |
| JPWO2002100833A1 (ja) * | 2001-06-12 | 2004-09-24 | 住友製薬株式会社 | Ｒｈｏキナーゼ阻害剤 |
| WO2006009889A1 (en) * | 2004-06-17 | 2006-01-26 | Smithkline Beecham Corporation | Novel inhibitors of rho-kinases |
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- 2004-06-18 AT AT04755699T patent/ATE532781T1/de active
- 2004-06-18 EP EP04755699A patent/EP1633740B1/en not_active Expired - Lifetime
- 2004-06-18 JP JP2006517466A patent/JP4869068B2/ja not_active Expired - Fee Related
- 2004-06-18 US US10/560,502 patent/US7560467B2/en not_active Expired - Fee Related
- 2004-06-18 ES ES04755699T patent/ES2374272T3/es not_active Expired - Lifetime
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