JP2012506848A5 - - Google Patents
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- JP2012506848A5 JP2012506848A5 JP2011532652A JP2011532652A JP2012506848A5 JP 2012506848 A5 JP2012506848 A5 JP 2012506848A5 JP 2011532652 A JP2011532652 A JP 2011532652A JP 2011532652 A JP2011532652 A JP 2011532652A JP 2012506848 A5 JP2012506848 A5 JP 2012506848A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- carboxamide
- dihydro
- pyrazole
- group
- 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.)
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- SYGSTRANUHFLOT-UHFFFAOYSA-N chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C1=CC=C2C3=NN=C(C(=O)N)C3=COC2=C1 SYGSTRANUHFLOT-UHFFFAOYSA-N 0.000 claims 57
- -1 NR 11 Inorganic materials 0.000 claims 48
- 125000000217 alkyl group Chemical group 0.000 claims 43
- 125000001188 haloalkyl group Chemical group 0.000 claims 40
- 229910052739 hydrogen Inorganic materials 0.000 claims 39
- 239000001257 hydrogen Substances 0.000 claims 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims 36
- 125000001589 carboacyl group Chemical group 0.000 claims 34
- 125000003118 aryl group Chemical group 0.000 claims 29
- 125000000623 heterocyclic group Chemical group 0.000 claims 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 28
- 229910052736 halogen Inorganic materials 0.000 claims 27
- 150000002367 halogens Chemical class 0.000 claims 27
- 125000003545 alkoxy group Chemical group 0.000 claims 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 23
- 125000001072 heteroaryl group Chemical group 0.000 claims 22
- 150000002431 hydrogen Chemical class 0.000 claims 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 17
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 14
- ABDMQSFNJPYOLA-UHFFFAOYSA-N NS(=O)(=O)[N+]([O-])=O Chemical compound NS(=O)(=O)[N+]([O-])=O ABDMQSFNJPYOLA-UHFFFAOYSA-N 0.000 claims 13
- 125000003342 alkenyl group Chemical group 0.000 claims 13
- 125000000304 alkynyl group Chemical group 0.000 claims 13
- 150000003857 carboxamides Chemical class 0.000 claims 13
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 13
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 150000001204 N-oxides Chemical class 0.000 claims 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 6
- 239000005711 Benzoic acid Substances 0.000 claims 5
- 235000010233 benzoic acid Nutrition 0.000 claims 5
- 125000002837 carbocyclic group Chemical group 0.000 claims 5
- 150000004702 methyl esters Chemical class 0.000 claims 4
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 claims 3
- 229910005965 SO 2 Inorganic materials 0.000 claims 3
- WWAFSLUZQOZZNF-UHFFFAOYSA-N cyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC=CC=C2C(C(=O)N)=NN=C21 WWAFSLUZQOZZNF-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- BDJZCHPNVIUIIM-UHFFFAOYSA-N 1-methyl-n-(6-methylpyridin-2-yl)-5-oxo-4h-pyrazolo[4,3-h]quinoline-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=NC=CC=C4C(=O)C3)N(C)N=2)=N1 BDJZCHPNVIUIIM-UHFFFAOYSA-N 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 125000004494 ethyl ester group Chemical group 0.000 claims 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- BMWWVNBXABDUCZ-UHFFFAOYSA-N 1,5,5-trimethyl-n-(6-methylpyridin-2-yl)-4h-pyrazolo[4,3-h]quinoline-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=NC=CC=C4C(C)(C)C3)N(C)N=2)=N1 BMWWVNBXABDUCZ-UHFFFAOYSA-N 0.000 claims 1
- QVMJSZASSYYWNQ-UHFFFAOYSA-N 1,5-dimethyl-n-(6-methylpyridin-2-yl)-4,6-dihydropyrazolo[4,3-d][2]benzazepine-3-carboxamide Chemical compound N=1N(C)C=2C3=CC=CC=C3CN(C)CC=2C=1C(=O)NC1=CC=CC(C)=N1 QVMJSZASSYYWNQ-UHFFFAOYSA-N 0.000 claims 1
- SADOTBOHBOXZQQ-UHFFFAOYSA-N 1,5-dimethyl-n-(6-methylpyridin-2-yl)-4h-pyrazolo[4,3-c][1,5]naphthyridine-3-carboxamide Chemical compound N=1N(C)C=2C3=NC=CC=C3N(C)CC=2C=1C(=O)NC1=CC=CC(C)=N1 SADOTBOHBOXZQQ-UHFFFAOYSA-N 0.000 claims 1
- AEYFLFNGIYIOJD-UHFFFAOYSA-N 1,5-dimethyl-n-(6-methylpyridin-2-yl)-4h-pyrazolo[4,3-c]quinoline-3-carboxamide Chemical compound N=1N(C)C=2C3=CC=CC=C3N(C)CC=2C=1C(=O)NC1=CC=CC(C)=N1 AEYFLFNGIYIOJD-UHFFFAOYSA-N 0.000 claims 1
- UNDPJXSVYCTQFB-UHFFFAOYSA-N 1,6-dimethyl-n-(6-methylpyridin-2-yl)-4,5-dihydropyrazolo[4,3-d][1]benzazepine-3-carboxamide Chemical compound N=1N(C)C=2C3=CC=CC=C3N(C)CCC=2C=1C(=O)NC1=CC=CC(C)=N1 UNDPJXSVYCTQFB-UHFFFAOYSA-N 0.000 claims 1
- RBBKQOZCKDADCQ-UHFFFAOYSA-N 1,8-dimethyl-n-(6-methylpyridin-2-yl)-4,5-dihydropyrazolo[4,3-h]quinoline-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=NC(C)=CC=C4CC3)N(C)N=2)=N1 RBBKQOZCKDADCQ-UHFFFAOYSA-N 0.000 claims 1
- NFHQWJXNGUPFHM-UHFFFAOYSA-N 1-ethyl-n-(6-methylpyridin-2-yl)-4,5-dihydropyrazolo[4,3-h]quinoline-3-carboxamide Chemical compound C1=2CCC3=CC=CN=C3C=2N(CC)N=C1C(=O)NC1=CC=CC(C)=N1 NFHQWJXNGUPFHM-UHFFFAOYSA-N 0.000 claims 1
- RYDADHAEBVEBCP-UHFFFAOYSA-N 1-methyl-3-[1-(6-methylpyridin-2-yl)azetidin-3-yl]-4,5-dihydropyrazolo[4,3-h]quinoline Chemical compound CC1=CC=CC(N2CC(C2)C=2C3=C(C4=NC=CC=C4CC3)N(C)N=2)=N1 RYDADHAEBVEBCP-UHFFFAOYSA-N 0.000 claims 1
- ZQSHHJVNWLVRCC-UHFFFAOYSA-N 1-methyl-3-[1-(6-methylpyridin-2-yl)ethoxy]-4,5-dihydropyrazolo[4,3-h]quinoline Chemical compound N=1N(C)C(C2=NC=CC=C2CC2)=C2C=1OC(C)C1=CC=CC(C)=N1 ZQSHHJVNWLVRCC-UHFFFAOYSA-N 0.000 claims 1
- BVUCKBPAWUTYNM-UHFFFAOYSA-N 1-methyl-N-(6-methylpyridin-2-yl)-5-oxo-4,6-dihydropyrazolo[4,3-d][1]benzazepine-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=CC=CC=C4NC(=O)C3)N(C)N=2)=N1 BVUCKBPAWUTYNM-UHFFFAOYSA-N 0.000 claims 1
- ZMZMFSAEQWTQMQ-UHFFFAOYSA-N 1-methyl-n-(1-methyl-5-phenylpyrrol-2-yl)-4,5-dihydropyrazolo[4,3-h]quinoline-3-carboxamide Chemical compound C1=2CCC3=CC=CN=C3C=2N(C)N=C1C(=O)NC(N1C)=CC=C1C1=CC=CC=C1 ZMZMFSAEQWTQMQ-UHFFFAOYSA-N 0.000 claims 1
- ANGKGBOGRLFDAQ-UHFFFAOYSA-N 1-methyl-n-(2-methylpyrimidin-4-yl)-4,5-dihydropyrazolo[4,3-h]quinoline-3-carboxamide Chemical compound CC1=NC=CC(NC(=O)C=2C3=C(C4=NC=CC=C4CC3)N(C)N=2)=N1 ANGKGBOGRLFDAQ-UHFFFAOYSA-N 0.000 claims 1
- BWTYAGFYBOUBMQ-UHFFFAOYSA-N 1-methyl-n-(5-methyl-1,2-oxazol-3-yl)-4h-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound O1C(C)=CC(NC(=O)C=2C3=C(C4=CC=CC=C4OC3)N(C)N=2)=N1 BWTYAGFYBOUBMQ-UHFFFAOYSA-N 0.000 claims 1
- OYGFTMJUTVUDQJ-UHFFFAOYSA-N 1-methyl-n-(6-methylpyrazin-2-yl)-4,5-dihydropyrazolo[4,3-h]quinoline-3-carboxamide Chemical compound CC1=CN=CC(NC(=O)C=2C3=C(C4=NC=CC=C4CC3)N(C)N=2)=N1 OYGFTMJUTVUDQJ-UHFFFAOYSA-N 0.000 claims 1
- AFPZYYYIVANXQT-UHFFFAOYSA-N 1-methyl-n-(6-methylpyridin-2-yl)-4,5-dihydropyrazolo[3,4-f]isoquinoline-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=CC=NC=C4CC3)N(C)N=2)=N1 AFPZYYYIVANXQT-UHFFFAOYSA-N 0.000 claims 1
- VMCMEOZNQTXBHQ-UHFFFAOYSA-N 1-methyl-n-(6-methylpyridin-2-yl)-4,5-dihydropyrazolo[3,4-f]quinoline-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=CC=CN=C4CC3)N(C)N=2)=N1 VMCMEOZNQTXBHQ-UHFFFAOYSA-N 0.000 claims 1
- RQZMLVWSFNGCLE-UHFFFAOYSA-N 1-methyl-n-(6-methylpyridin-2-yl)-4,5-dihydropyrazolo[3,4-f]quinoxaline-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=NC=CN=C4CC3)N(C)N=2)=N1 RQZMLVWSFNGCLE-UHFFFAOYSA-N 0.000 claims 1
- YVQFXQUHGOALOJ-UHFFFAOYSA-N 1-methyl-n-(6-methylpyridin-2-yl)-4,5-dihydropyrazolo[4,3-h]isoquinoline-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=CN=CC=C4CC3)N(C)N=2)=N1 YVQFXQUHGOALOJ-UHFFFAOYSA-N 0.000 claims 1
- PPFQPJIMARWLRA-UHFFFAOYSA-N 1-methyl-n-(6-methylpyridin-2-yl)-4,5-dihydropyrazolo[4,3-h]quinolin-3-amine Chemical compound CC1=CC=CC(NC=2C3=C(C4=NC=CC=C4CC3)N(C)N=2)=N1 PPFQPJIMARWLRA-UHFFFAOYSA-N 0.000 claims 1
- SJWIAQHMFLXKRF-UHFFFAOYSA-N 1-methyl-n-(6-methylpyridin-2-yl)-4,5-dihydropyrazolo[4,3-h]quinoline-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=NC=CC=C4CC3)N(C)N=2)=N1 SJWIAQHMFLXKRF-UHFFFAOYSA-N 0.000 claims 1
- ONBSDUFTCWELTF-UHFFFAOYSA-N 1-methyl-n-(6-methylpyridin-2-yl)-4h-imidazo[5,1-c][1,4]benzoxazine-3-carboxamide Chemical compound C=12COC3=CC=CC=C3N2C(C)=NC=1C(=O)NC1=CC=CC(C)=N1 ONBSDUFTCWELTF-UHFFFAOYSA-N 0.000 claims 1
- XHRNDTVWNKFFQE-UHFFFAOYSA-N 1-methyl-n-(6-methylpyridin-2-yl)-5,6-dihydro-4h-pyrazolo[4,3-d][2]benzazepine-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=CC=CC=C4CNC3)N(C)N=2)=N1 XHRNDTVWNKFFQE-UHFFFAOYSA-N 0.000 claims 1
- HPBATAXLRYKBBV-UHFFFAOYSA-N 1-methyl-n-(6-methylpyridin-2-yl)-5-oxo-4h-pyrazolo[4,3-c]isoquinoline-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=CC=CC=C4C(=O)N3)N(C)N=2)=N1 HPBATAXLRYKBBV-UHFFFAOYSA-N 0.000 claims 1
- WSTRYTWRTPRJCG-UHFFFAOYSA-N 1-methyl-n-(6-methylpyridin-2-yl)-6-oxo-4,5-dihydropyrazolo[4,3-d][2]benzazepine-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=CC=CC=C4C(=O)NC3)N(C)N=2)=N1 WSTRYTWRTPRJCG-UHFFFAOYSA-N 0.000 claims 1
- SUSYSDXOYROVQP-UHFFFAOYSA-N 1-methyl-n-[1-(6-methylpyridin-2-yl)ethyl]-4,5-dihydropyrazolo[4,3-h]quinolin-3-amine Chemical compound N=1N(C)C(C2=NC=CC=C2CC2)=C2C=1NC(C)C1=CC=CC(C)=N1 SUSYSDXOYROVQP-UHFFFAOYSA-N 0.000 claims 1
- VXHHQRYFORKPDE-UHFFFAOYSA-N 1-methyl-n-[3-(trifluoromethyl)phenyl]-4h-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C1=2COC3=CC=CC=C3C=2N(C)N=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 VXHHQRYFORKPDE-UHFFFAOYSA-N 0.000 claims 1
- CFSAZOCKLWHLCY-UHFFFAOYSA-N 1-methyl-n-[6-(trifluoromethyl)pyridin-2-yl]-4,5-dihydropyrazolo[4,3-h]quinoline-3-carboxamide Chemical compound C1=2CCC3=CC=CN=C3C=2N(C)N=C1C(=O)NC1=CC=CC(C(F)(F)F)=N1 CFSAZOCKLWHLCY-UHFFFAOYSA-N 0.000 claims 1
- IWGREDKROULLQB-UHFFFAOYSA-N 2,3-dihydro-1,4-benzoxazin-4-yl-(1-methyl-4h-chromeno[4,3-c]pyrazol-3-yl)methanone Chemical compound C1OC2=CC=CC=C2C2=C1C(C(=O)N1C3=CC=CC=C3OCC1)=NN2C IWGREDKROULLQB-UHFFFAOYSA-N 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- BSTZOEXIXQXOKE-UHFFFAOYSA-N 2-[3,5-bis(methoxycarbonyl)phenoxy]acetic acid Chemical compound COC(=O)C1=CC(OCC(O)=O)=CC(C(=O)OC)=C1 BSTZOEXIXQXOKE-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- ADRRIUGXSOGPPW-UHFFFAOYSA-N 2h-oxazine-3-carboxamide Chemical compound NC(=O)C1=CC=CON1 ADRRIUGXSOGPPW-UHFFFAOYSA-N 0.000 claims 1
- SOWHODROPZJSNW-UHFFFAOYSA-N 3,9-dimethyl-N-(6-methylpyridin-2-yl)-3,4,9,14-tetrazatricyclo[8.4.0.02,6]tetradeca-1(10),2(6),4,11,13-pentaene-5-carboxamide Chemical compound N=1N(C)C=2C3=NC=CC=C3N(C)CCC=2C=1C(=O)NC1=CC=CC(C)=N1 SOWHODROPZJSNW-UHFFFAOYSA-N 0.000 claims 1
- BEZIZNWRCABQHZ-UHFFFAOYSA-N 3-[1-(3-chlorophenoxy)ethyl]-1-methyl-4,5-dihydropyrazolo[4,3-h]quinoline Chemical compound N=1N(C)C(C2=NC=CC=C2CC2)=C2C=1C(C)OC1=CC=CC(Cl)=C1 BEZIZNWRCABQHZ-UHFFFAOYSA-N 0.000 claims 1
- COXFKPXHIYSYBU-UHFFFAOYSA-N 3-[2-(3-chlorophenoxy)propan-2-yl]-1-methyl-4,5-dihydropyrazolo[4,3-h]quinoline Chemical compound C1=2CCC3=CC=CN=C3C=2N(C)N=C1C(C)(C)OC1=CC=CC(Cl)=C1 COXFKPXHIYSYBU-UHFFFAOYSA-N 0.000 claims 1
- IXUINHVZQQJJBW-UHFFFAOYSA-N 3-chloro-n-[(1-methyl-4h-chromeno[4,3-c]pyrazol-3-yl)methyl]aniline Chemical compound C1=2COC3=CC=CC=C3C=2N(C)N=C1CNC1=CC=CC(Cl)=C1 IXUINHVZQQJJBW-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- RRLMDJWUEMMKQJ-UHFFFAOYSA-N 5,5-difluoro-1-methyl-n-(6-methylpyridin-2-yl)-4h-benzo[g]indazole-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=CC=CC=C4C(F)(F)C3)N(C)N=2)=N1 RRLMDJWUEMMKQJ-UHFFFAOYSA-N 0.000 claims 1
- ZTFWZGDQXXWKJL-UHFFFAOYSA-N 5,5-difluoro-1-methyl-n-(6-methylpyridin-2-yl)-4h-pyrazolo[4,3-h]quinoline-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=NC=CC=C4C(F)(F)C3)N(C)N=2)=N1 ZTFWZGDQXXWKJL-UHFFFAOYSA-N 0.000 claims 1
- VNYHFICCURNDMT-UHFFFAOYSA-N 5-acetyl-n-(3-chlorophenyl)-1-methyl-4h-pyrazolo[4,3-c]quinoline-3-carboxamide Chemical compound N=1N(C)C=2C3=CC=CC=C3N(C(=O)C)CC=2C=1C(=O)NC1=CC=CC(Cl)=C1 VNYHFICCURNDMT-UHFFFAOYSA-N 0.000 claims 1
- YZDPQURRCKRDAY-UHFFFAOYSA-N 5-hydroxy-1-methyl-n-(6-methylpyridin-2-yl)-4,5-dihydrobenzo[g]indazole-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=CC=CC=C4C(O)C3)N(C)N=2)=N1 YZDPQURRCKRDAY-UHFFFAOYSA-N 0.000 claims 1
- BZWSVKXIMIDJKU-UHFFFAOYSA-N 5-hydroxy-1-methyl-n-(6-methylpyridin-2-yl)-4,5-dihydropyrazolo[4,3-h]quinoline-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=NC=CC=C4C(O)C3)N(C)N=2)=N1 BZWSVKXIMIDJKU-UHFFFAOYSA-N 0.000 claims 1
- QNXNGFXTUWDTSK-UHFFFAOYSA-N 6,6-difluoro-1-methyl-n-(6-methylpyridin-2-yl)-4,5,7,8-tetrahydrocyclohepta[g]indazole-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=C(C(CCC=C4)(F)F)CC3)N(C)N=2)=N1 QNXNGFXTUWDTSK-UHFFFAOYSA-N 0.000 claims 1
- PUHYAVUGRCGNBE-UHFFFAOYSA-N 6-cyclopropyl-n-[1-(1-methyl-4,5-dihydropyrazolo[4,3-h]quinolin-3-yl)ethyl]pyridin-2-amine Chemical compound N=1N(C)C(C2=NC=CC=C2CC2)=C2C=1C(C)NC(N=1)=CC=CC=1C1CC1 PUHYAVUGRCGNBE-UHFFFAOYSA-N 0.000 claims 1
- GWOXUDYJXOFPQN-UHFFFAOYSA-N 6-fluoro-1-methyl-n-(6-methylpyridin-2-yl)-4,5-dihydropyrazolo[4,3-h]quinoline-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=NC=CC(F)=C4CC3)N(C)N=2)=N1 GWOXUDYJXOFPQN-UHFFFAOYSA-N 0.000 claims 1
- JVEKVBAKDDEFBR-UHFFFAOYSA-N 6-hydroxy-1-methyl-n-(6-methylpyridin-2-yl)-5,6,7,8-tetrahydro-4h-cyclohepta[g]indazole-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=C(C(CCC=C4)O)CC3)N(C)N=2)=N1 JVEKVBAKDDEFBR-UHFFFAOYSA-N 0.000 claims 1
- OFYMVWIGPPQIEP-UHFFFAOYSA-N 6-methyl-n-[2-(1-methyl-4,5-dihydropyrazolo[4,3-h]quinolin-3-yl)propan-2-yl]pyridin-2-amine Chemical compound CC1=CC=CC(NC(C)(C)C=2C3=C(C4=NC=CC=C4CC3)N(C)N=2)=N1 OFYMVWIGPPQIEP-UHFFFAOYSA-N 0.000 claims 1
- SNTAARZVDYYKHG-UHFFFAOYSA-N 7-fluoro-1-methyl-n-(6-methylpyridin-2-yl)-4,5-dihydropyrazolo[4,3-h]quinoline-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=NC=C(F)C=C4CC3)N(C)N=2)=N1 SNTAARZVDYYKHG-UHFFFAOYSA-N 0.000 claims 1
- BVZUESLWPSNZAB-UHFFFAOYSA-N 7-fluoro-1-methyl-n-(6-methylpyridin-2-yl)-4h-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=C(C4=CC=C(F)C=C4OC3)N(C)N=2)=N1 BVZUESLWPSNZAB-UHFFFAOYSA-N 0.000 claims 1
- SXEYEWRZLARJEO-UHFFFAOYSA-N 8-chloro-n-(3-chlorophenyl)-1-methyl-4h-chromeno[4,3-c]pyrazole-3-carboxamide Chemical compound C1=2COC3=CC=C(Cl)C=C3C=2N(C)N=C1C(=O)NC1=CC=CC(Cl)=C1 SXEYEWRZLARJEO-UHFFFAOYSA-N 0.000 claims 1
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| WO2011151361A1 (en) * | 2010-06-03 | 2011-12-08 | Glaxo Group Limited | Novel compounds |
| RU2663898C2 (ru) | 2013-06-24 | 2018-08-13 | Мерк Патент Гмбх | Пиразольные соединения в качестве модуляторов fshr и их применение |
| EP3288948B1 (en) * | 2015-04-30 | 2019-11-20 | Novartis AG | Fused tricyclic pyrazole derivatives useful for modulating farnesoid x receptors |
| DK3341376T3 (da) | 2015-08-26 | 2021-03-29 | Fundacion Del Sector Publico Estatal Centro Nac De Investigaciones Oncologicas Carlos Iii F S P Cnio | Kondenserede tricykliske forbindelser som proteinkinase-inhibitorer |
| BR112018074231A2 (pt) * | 2016-05-25 | 2019-03-06 | Akarna Therapeutics, Ltd. | compostos bicíclicos fundidos para o tratamento de doença |
| US11530218B2 (en) | 2020-01-20 | 2022-12-20 | Incyte Corporation | Spiro compounds as inhibitors of KRAS |
| US11739102B2 (en) | 2020-05-13 | 2023-08-29 | Incyte Corporation | Fused pyrimidine compounds as KRAS inhibitors |
| US11999752B2 (en) | 2020-08-28 | 2024-06-04 | Incyte Corporation | Vinyl imidazole compounds as inhibitors of KRAS |
| US11767320B2 (en) | 2020-10-02 | 2023-09-26 | Incyte Corporation | Bicyclic dione compounds as inhibitors of KRAS |
| WO2022204112A1 (en) | 2021-03-22 | 2022-09-29 | Incyte Corporation | Imidazole and triazole kras inhibitors |
| US12441727B2 (en) | 2021-07-07 | 2025-10-14 | Incyte Corporation | Tricyclic compounds as inhibitors of KRAS |
| JP2024534187A (ja) | 2021-08-31 | 2024-09-18 | インサイト・コーポレイション | Ｋｒａｓの阻害剤としてのナフチリジン化合物 |
| WO2023049697A1 (en) | 2021-09-21 | 2023-03-30 | Incyte Corporation | Hetero-tricyclic compounds as inhibitors of kras |
| JP2024537824A (ja) | 2021-10-01 | 2024-10-16 | インサイト・コーポレイション | ピラゾロキノリンｋｒａｓ阻害剤 |
| PE20242113A1 (es) | 2021-10-14 | 2024-10-28 | Incyte Corp | Compuestos de quinolina como inhibidores de kras |
| WO2023077046A1 (en) | 2021-10-29 | 2023-05-04 | Arcus Biosciences, Inc. | Inhibitors of hif-2alpha and methods of use thereof |
| WO2024044778A2 (en) * | 2022-08-26 | 2024-02-29 | Celmatix Inc. | Novel modulators of fshr and uses thereof |
| CN120682241A (zh) * | 2024-03-22 | 2025-09-23 | 复旦大学附属中山医院 | 三环骨架化合物及其在制备抗肿瘤药物中的应用 |
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| GB9318691D0 (en) * | 1993-09-09 | 1993-10-27 | Merck Sharp & Dohme | Therapeutic agents |
| EP1427706B1 (en) * | 2001-09-19 | 2007-05-30 | Pharmacia Corporation | Substituted pyrazolo compounds for the treatment of inflammation |
| US20060281803A1 (en) * | 2003-09-23 | 2006-12-14 | Lindsley Craig W | Pyrazole modulators of metabotropic glutamate receptors |
| WO2008035356A2 (en) * | 2006-09-20 | 2008-03-27 | Glenmark Pharmaceuticals Limited | Novel cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| WO2009010824A1 (en) * | 2007-07-13 | 2009-01-22 | Glenmark Pharmaceuticals, S.A. | Dihydrochromenopyrazole derivatives as vanilloid receptor ligands |
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- 2009-10-23 EP EP09740889A patent/EP2346832A1/en not_active Withdrawn
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- 2009-10-23 WO PCT/EP2009/064015 patent/WO2010049366A1/en not_active Ceased
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