JP2014533745A5

JP2014533745A5 -

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Publication number: JP2014533745A5
Authority: JP; Japan
Prior art keywords: chloro; phenyl; methyl; dihydro; pyrazol
Prior art date: 2012-11-28
Legal status : Granted

Application number

JP2014544018A

Other languages

English (en)

Japanese (ja)

Other versions

JP5992054B2 (ja

JP2014533745A (ja

Filing date

2012-11-28

Publication date

2016-01-21

2012-11-28 Application filed filed Critical

2012-11-28 Priority claimed from PCT/IB2012/056796 external-priority patent/WO2013080141A1/en

2014-12-15 Publication of JP2014533745A publication Critical patent/JP2014533745A/ja

2016-01-21 Publication of JP2014533745A5 publication Critical patent/JP2014533745A5/ja

2016-09-14 Application granted granted Critical

2016-09-14 Publication of JP5992054B2 publication Critical patent/JP5992054B2/ja

Status Expired - Fee Related legal-status Critical Current

2032-11-28 Anticipated expiration legal-status Critical

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-1 —C (O) OH Chemical group 0.000 claims description 105
125000000217 alkyl group Chemical group 0.000 claims description 103
150000003839 salts Chemical class 0.000 claims description 50
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 36
125000005843 halogen group Chemical group 0.000 claims description 35
125000001424 substituent group Chemical group 0.000 claims description 35
150000001875 compounds Chemical class 0.000 claims description 34
125000000623 heterocyclic group Chemical group 0.000 claims description 27
125000003545 alkoxy group Chemical group 0.000 claims description 26
125000004093 cyano group Chemical group *C#N 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
125000001072 heteroaryl group Chemical group 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 9
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
125000002950 monocyclic group Chemical group 0.000 claims description 9
102000012199 E3 ubiquitin-protein ligase Mdm2 Human genes 0.000 claims description 8
108050002772 E3 ubiquitin-protein ligase Mdm2 Proteins 0.000 claims description 8
102000017274 MDM4 Human genes 0.000 claims description 8
108050005300 MDM4 Proteins 0.000 claims description 8
230000000694 effects Effects 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
150000001721 carbon Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
201000010099 disease Diseases 0.000 claims description 6
208000035475 disorder Diseases 0.000 claims description 6
230000001404 mediated effect Effects 0.000 claims description 6
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
AYJVXDFOPGRLNI-QHCPKHFHSA-N (4s)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chloro-2-methylphenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2[C@H](C=3C(=CC(Cl)=CC=3)C)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 AYJVXDFOPGRLNI-QHCPKHFHSA-N 0.000 claims description 4
YDAUQLMQAVQZLU-UHFFFAOYSA-N 4-(4-chloro-3-fluorophenyl)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(Cl)=CC=3)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 YDAUQLMQAVQZLU-UHFFFAOYSA-N 0.000 claims description 4
RQRGUXOSYRMAOC-DEOSSOPVSA-N 4-[(4s)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2[C@H](C=3C=CC(=CC=3)C#N)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 RQRGUXOSYRMAOC-DEOSSOPVSA-N 0.000 claims description 4
RSRIVJZZBKJDKL-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]-3-fluorobenzonitrile Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C(=CC(=CC=3)C#N)F)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 RSRIVJZZBKJDKL-UHFFFAOYSA-N 0.000 claims description 4
RQRGUXOSYRMAOC-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(=CC=3)C#N)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 RQRGUXOSYRMAOC-UHFFFAOYSA-N 0.000 claims description 4
AYJVXDFOPGRLNI-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chloro-2-methylphenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 AYJVXDFOPGRLNI-UHFFFAOYSA-N 0.000 claims description 4
OIFYSZRTTNMVQD-UHFFFAOYSA-N 5-(5-chloro-2-oxo-1h-pyridin-3-yl)-4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(NC=C(Cl)C=3)=O)C(=O)C2=N1 OIFYSZRTTNMVQD-UHFFFAOYSA-N 0.000 claims description 4
IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 claims description 4
IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
SJSSRJQZFGJFOX-QFIPXVFZSA-N (4s)-5-(5-chloro-2-oxo-1h-pyridin-3-yl)-4-(4-chlorophenyl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2[C@H](C=3C=CC(Cl)=CC=3)N(C=3C(NC=C(Cl)C=3)=O)C(=O)C2=N1 SJSSRJQZFGJFOX-QFIPXVFZSA-N 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 claims description 2
YOXSWOWVTGKRRI-XYXHBKGXSA-N (2s)-2-[[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]methyl]-n,n-dimethylpyrrolidine-1-carboxamide Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1C[C@@H]1CCCN1C(=O)N(C)C YOXSWOWVTGKRRI-XYXHBKGXSA-N 0.000 claims description 2
MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 claims description 2
SJSSRJQZFGJFOX-JOCHJYFZSA-N (4R)-5-(5-chloro-2-oxo-1H-pyridin-3-yl)-4-(4-chlorophenyl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-3-propan-2-yl-4H-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COc1nc(ncc1-n1nc2C(=O)N([C@@H](c2c1C(C)C)c1ccc(Cl)cc1)c1cc(Cl)c[nH]c1=O)N(C)C SJSSRJQZFGJFOX-JOCHJYFZSA-N 0.000 claims description 2
ZPZFPPPXKLFRBC-MUUNZHRXSA-N (4r)-4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2[C@@H](C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 ZPZFPPPXKLFRBC-MUUNZHRXSA-N 0.000 claims description 2
HMHZLUVFZNQBTE-JOCHJYFZSA-N (4r)-5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(2-hydroxyethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound N1([C@@H](C2=C(N(N=C2C1=O)CCO)C(C)C)C=1C(=CC(Cl)=CC=1)C)C1=CC=CC(Cl)=C1F HMHZLUVFZNQBTE-JOCHJYFZSA-N 0.000 claims description 2
AYJVXDFOPGRLNI-HSZRJFAPSA-N (4r)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chloro-2-methylphenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2[C@@H](C=3C(=CC(Cl)=CC=3)C)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 AYJVXDFOPGRLNI-HSZRJFAPSA-N 0.000 claims description 2
ZPZFPPPXKLFRBC-NDEPHWFRSA-N (4s)-4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2[C@H](C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 ZPZFPPPXKLFRBC-NDEPHWFRSA-N 0.000 claims description 2
HMHZLUVFZNQBTE-QFIPXVFZSA-N (4s)-5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(2-hydroxyethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound N1([C@H](C2=C(N(N=C2C1=O)CCO)C(C)C)C=1C(=CC(Cl)=CC=1)C)C1=CC=CC(Cl)=C1F HMHZLUVFZNQBTE-QFIPXVFZSA-N 0.000 claims description 2
YBMQYNARIZUNIO-HKBQPEDESA-N (4s)-5-[5-chloro-2-[2-(dimethylamino)ethoxy]phenyl]-4-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2[C@H](C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)OCCN(C)C)C(=O)C2=N1 YBMQYNARIZUNIO-HKBQPEDESA-N 0.000 claims description 2
ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 claims description 2
MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 claims description 2
APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 claims description 2
ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 claims description 2
DZWXCJZDTKKTNU-UHFFFAOYSA-N 2-[(1-acetyl-4-hydroxypiperidin-4-yl)methyl]-4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC1(O)CCN(C(C)=O)CC1 DZWXCJZDTKKTNU-UHFFFAOYSA-N 0.000 claims description 2
QZPHTHGRGSOROE-UHFFFAOYSA-N 2-[(1-acetylpiperidin-4-yl)methyl]-4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC1CCN(C(C)=O)CC1 QZPHTHGRGSOROE-UHFFFAOYSA-N 0.000 claims description 2
YBBQYZSRNHSUCI-UHFFFAOYSA-N 2-[2-(4-acetylpiperazin-1-yl)-2-oxoethyl]-4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC(=O)N1CCN(C(C)=O)CC1 YBBQYZSRNHSUCI-UHFFFAOYSA-N 0.000 claims description 2
IQXKRKFNNIJHKM-UHFFFAOYSA-N 2-[2-[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]ethyl]isoindole-1,3-dione Chemical compound O=C1C2=NN(CCN3C(C4=CC=CC=C4C3=O)=O)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC=CC(Cl)=C1F IQXKRKFNNIJHKM-UHFFFAOYSA-N 0.000 claims description 2
YEQFUJXHFVNFLD-UHFFFAOYSA-N 2-[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-n-methylacetamide Chemical compound C12=C(C(C)C)N(CC(=O)NC)N=C2C(=O)N(C=2C(=C(Cl)C=CC=2)F)C1C1=CC=C(Cl)C=C1C YEQFUJXHFVNFLD-UHFFFAOYSA-N 0.000 claims description 2
ZJWOFSLLBIUKPW-UHFFFAOYSA-N 2-[5-(aminomethyl)-2-methoxyphenyl]-4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=C(CN)C=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 ZJWOFSLLBIUKPW-UHFFFAOYSA-N 0.000 claims description 2
DLKYKILDEXFUBY-UHFFFAOYSA-N 2-[5-(aminomethyl)-2-methoxyphenyl]-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chloro-2-methylphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=C(CN)C=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 DLKYKILDEXFUBY-UHFFFAOYSA-N 0.000 claims description 2
JZFAHAGJOFEDPR-XYXHBKGXSA-N 2-[[(2s)-1-acetylpyrrolidin-2-yl]methyl]-4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1C[C@@H]1CCCN1C(C)=O JZFAHAGJOFEDPR-XYXHBKGXSA-N 0.000 claims description 2
KQFUYAPAPGFYMI-UHFFFAOYSA-N 2-[[4-(4-chlorophenyl)-5-(3,4-difluorophenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]methyl]benzonitrile Chemical compound CC(C)C1=C2C(C=3C=CC(Cl)=CC=3)N(C=3C=C(F)C(F)=CC=3)C(=O)C2=NN1CC1=CC=CC=C1C#N KQFUYAPAPGFYMI-UHFFFAOYSA-N 0.000 claims description 2
AVTJOXSIUYDNFU-UHFFFAOYSA-N 2-benzyl-4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC1=CC=CC=C1 AVTJOXSIUYDNFU-UHFFFAOYSA-N 0.000 claims description 2
WPSSCIDRUBTKAN-UHFFFAOYSA-N 2-benzyl-5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1CC1=CC=CC=C1 WPSSCIDRUBTKAN-UHFFFAOYSA-N 0.000 claims description 2
125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
ALBXXUZUKJRRRW-UHFFFAOYSA-N 3-(1-aminopropan-2-yl)-5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)CN)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=N1 ALBXXUZUKJRRRW-UHFFFAOYSA-N 0.000 claims description 2
HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 claims description 2
BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 claims description 2
WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 claims description 2
SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 claims description 2
RCVRAHVEDDYMCE-UHFFFAOYSA-N 3-[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-4-methoxy-n,n-dimethylbenzamide Chemical compound COC1=CC=C(C(=O)N(C)C)C=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 RCVRAHVEDDYMCE-UHFFFAOYSA-N 0.000 claims description 2
YVYATCZGDDDVSH-UHFFFAOYSA-N 3-[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-4-methoxy-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound COC1=CC=C(C(=O)NCCN2CCCC2)C=C1N(C(=C12)C(C)C)N=C1C(=O)N(C=1C(=CC=C(Cl)C=1)C)C2C1=CC=C(Cl)C=C1C YVYATCZGDDDVSH-UHFFFAOYSA-N 0.000 claims description 2
WKMPZXXAZAQLQZ-UHFFFAOYSA-N 3-[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-4-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(OC)C(N2C(=C3C(N(C(=O)C3=N2)C=2C(=CC=C(Cl)C=2)C)C=2C(=CC(Cl)=CC=2)C)C(C)C)=C1 WKMPZXXAZAQLQZ-UHFFFAOYSA-N 0.000 claims description 2
RUFLPMXZYPSUOV-UHFFFAOYSA-N 3-[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]benzonitrile Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C1=CC=CC(C#N)=C1 RUFLPMXZYPSUOV-UHFFFAOYSA-N 0.000 claims description 2
LFWZYTLMZYUEFQ-UHFFFAOYSA-N 3-[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]propanenitrile Chemical compound O=C1C2=NN(CCC#N)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC=CC(Cl)=C1F LFWZYTLMZYUEFQ-UHFFFAOYSA-N 0.000 claims description 2
JGDWYYYDKDRIQZ-UHFFFAOYSA-N 3-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-4-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(OC)C(N2C(=C3C(N(C(=O)C3=N2)C2=CN(C)C(=O)C(Cl)=C2)C=2C(=CC(Cl)=CC=2)C)C(C)C)=C1 JGDWYYYDKDRIQZ-UHFFFAOYSA-N 0.000 claims description 2
PMPUDZCQKFOGSX-UHFFFAOYSA-N 3-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 PMPUDZCQKFOGSX-UHFFFAOYSA-N 0.000 claims description 2
FTDQXIOMMPGVAT-UHFFFAOYSA-N 3-[5-(5-chloro-2-methylphenyl)-4-(4-cyanophenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1N1C(C(C)C)=C2C(C=3C=CC(=CC=3)C#N)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 FTDQXIOMMPGVAT-UHFFFAOYSA-N 0.000 claims description 2
CRWXYYDAMBWTKL-UHFFFAOYSA-N 3-[5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4-[4-(trifluoromethyl)phenyl]-4h-pyrrolo[3,4-c]pyrazol-2-yl]-n,4-dimethylbenzamide Chemical compound CNC(=O)C1=CC=C(C)C(N2C(=C3C(N(C(=O)C3=N2)C=2C(=CC=C(Cl)C=2)C)C=2C=CC(=CC=2)C(F)(F)F)C(C)C)=C1 CRWXYYDAMBWTKL-UHFFFAOYSA-N 0.000 claims description 2
BRWVYJDPNFVUHE-UHFFFAOYSA-N 3-chloro-5-[4-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-5-yl]benzonitrile Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C=C(C=C(Cl)C=3)C#N)C(=O)C2=N1 BRWVYJDPNFVUHE-UHFFFAOYSA-N 0.000 claims description 2
NFPQHOKNWHJKMC-UHFFFAOYSA-N 3-tert-butyl-5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-2,4-dihydropyrrolo[3,4-c]pyrazol-6-one Chemical compound C12=C(C(C)(C)C)NN=C2C(=O)N(C=2C(=C(Cl)C=CC=2)F)C1C1=CC=C(Cl)C=C1 NFPQHOKNWHJKMC-UHFFFAOYSA-N 0.000 claims description 2
KRKJHAZDWLVODZ-UHFFFAOYSA-N 4-(4-chloro-2-fluorophenyl)-5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)F)N(C=3C(N(C)C=C(Cl)C=3)=O)C(=O)C2=N1 KRKJHAZDWLVODZ-UHFFFAOYSA-N 0.000 claims description 2
RIGFJBPAOUYYDK-UHFFFAOYSA-N 4-(4-chloro-2-fluorophenyl)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)F)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 RIGFJBPAOUYYDK-UHFFFAOYSA-N 0.000 claims description 2
LQFQEWGXGDBOGP-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(2-chloropyridin-4-yl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C=C(Cl)N=CC=3)C(=O)C2=N1 LQFQEWGXGDBOGP-UHFFFAOYSA-N 0.000 claims description 2
GNUPSFNBJBWYRB-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(1-methylpiperidin-4-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1C1CCN(C)CC1 GNUPSFNBJBWYRB-UHFFFAOYSA-N 0.000 claims description 2
HWOBQJWTOBDSQY-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(2,3-dihydroxypropyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound O=C1C2=NN(CC(O)CO)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC(Cl)=CC=C1C HWOBQJWTOBDSQY-UHFFFAOYSA-N 0.000 claims description 2
FMTUQXWHYUZQKX-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 FMTUQXWHYUZQKX-UHFFFAOYSA-N 0.000 claims description 2
VWMHDGDJQMBFHU-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(2-methoxyethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound C12=C(C(C)C)N(CCOC)N=C2C(=O)N(C=2C(=CC=C(Cl)C=2)C)C1C1=CC=C(Cl)C=C1C VWMHDGDJQMBFHU-UHFFFAOYSA-N 0.000 claims description 2
ZPZFPPPXKLFRBC-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 ZPZFPPPXKLFRBC-UHFFFAOYSA-N 0.000 claims description 2
MIGFPEUHNSPEGD-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(4-methoxypyridin-3-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=NC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 MIGFPEUHNSPEGD-UHFFFAOYSA-N 0.000 claims description 2
MVJPAODGJWVCNG-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(4-methylpiperazine-1-carbonyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1C(=O)N1CCN(C)CC1 MVJPAODGJWVCNG-UHFFFAOYSA-N 0.000 claims description 2
BSYBXKOGLZBSHD-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(oxiran-2-ylmethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC1CO1 BSYBXKOGLZBSHD-UHFFFAOYSA-N 0.000 claims description 2
KZKVSNXVFALSMC-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(oxolan-2-ylmethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC1CCCO1 KZKVSNXVFALSMC-UHFFFAOYSA-N 0.000 claims description 2
IRWCMXNZTJROFT-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-[2-(2-oxopyrrolidin-1-yl)ethyl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CCN1CCCC1=O IRWCMXNZTJROFT-UHFFFAOYSA-N 0.000 claims description 2
IIZXQQZRRXYLSE-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-[2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC(=O)N1CCC(O)CC1 IIZXQQZRRXYLSE-UHFFFAOYSA-N 0.000 claims description 2
UNZCOOAPYFTFKR-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-[2-(4-methylpiperazin-1-yl)ethyl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CCN1CCN(C)CC1 UNZCOOAPYFTFKR-UHFFFAOYSA-N 0.000 claims description 2
DBEMYIHLOZGDDF-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-[2-oxo-2-(3-oxopiperazin-1-yl)ethyl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC(=O)N1CCNC(=O)C1 DBEMYIHLOZGDDF-UHFFFAOYSA-N 0.000 claims description 2
PSCSHVNMQAGNHC-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-3-propan-2-yl-2-(pyridin-2-ylmethyl)-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC1=CC=CC=N1 PSCSHVNMQAGNHC-UHFFFAOYSA-N 0.000 claims description 2
YDPLGSFJBCHSDW-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-n-methyl-6-oxo-n-phenyl-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazole-2-carboxamide Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1C(=O)N(C)C1=CC=CC=C1 YDPLGSFJBCHSDW-UHFFFAOYSA-N 0.000 claims description 2
DQKSQGUSULGQMU-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloropyridin-3-yl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C=C(Cl)C=NC=3)C(=O)C2=N1 DQKSQGUSULGQMU-UHFFFAOYSA-N 0.000 claims description 2
RNZZSMCPSZIPLM-UHFFFAOYSA-N 4-(4-chloro-3-fluorophenyl)-5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(Cl)=CC=3)N(C=3C(N(C)C=C(Cl)C=3)=O)C(=O)C2=N1 RNZZSMCPSZIPLM-UHFFFAOYSA-N 0.000 claims description 2
SPSDWBLEDCVGLA-UHFFFAOYSA-N 4-(4-chloro-3-fluorophenyl)-5-(5-chloro-2-oxo-1h-pyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(Cl)=CC=3)N(C=3C(NC=C(Cl)C=3)=O)C(=O)C2=N1 SPSDWBLEDCVGLA-UHFFFAOYSA-N 0.000 claims description 2
OZTFXLSOURVIGT-UHFFFAOYSA-N 4-(4-chloro-3-fluorophenyl)-5-(5-chloro-6-oxo-1h-pyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(Cl)=CC=3)N(C=3C=C(Cl)C(=O)NC=3)C(=O)C2=N1 OZTFXLSOURVIGT-UHFFFAOYSA-N 0.000 claims description 2
BQVXYVMHLPJQST-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-5-(1,5-dimethyl-2-oxopyridin-3-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(N(C)C=C(C)C=3)=O)C(=O)C2=N1 BQVXYVMHLPJQST-UHFFFAOYSA-N 0.000 claims description 2
IKDAKUWICQIDSR-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-5-(1,5-dimethyl-2-oxopyridin-3-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(N(C)C=C(C)C=3)=O)C(=O)C2=N1 IKDAKUWICQIDSR-UHFFFAOYSA-N 0.000 claims description 2
RZBALPLOLRLLGL-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(3,4-difluorophenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C=C(F)C(F)=CC=3)C(=O)C2=N1 RZBALPLOLRLLGL-UHFFFAOYSA-N 0.000 claims description 2
LXVKCNFEVHJFNO-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-[5-chloro-2-(2h-tetrazol-5-ylmethoxy)phenyl]-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=CC=C(Cl)C=3)OCC3=NNN=N3)C(=O)C2=N1 LXVKCNFEVHJFNO-UHFFFAOYSA-N 0.000 claims description 2
RQRGUXOSYRMAOC-XMMPIXPASA-N 4-[(4r)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2[C@@H](C=3C=CC(=CC=3)C#N)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 RQRGUXOSYRMAOC-XMMPIXPASA-N 0.000 claims description 2
VFMRTUQQYDQOGC-HSZRJFAPSA-N 4-[(4r)-5-(5-chloro-2-oxo-1h-pyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2[C@@H](C=3C=CC(=CC=3)C#N)N(C=3C(NC=C(Cl)C=3)=O)C(=O)C2=N1 VFMRTUQQYDQOGC-HSZRJFAPSA-N 0.000 claims description 2
VFMRTUQQYDQOGC-QHCPKHFHSA-N 4-[(4s)-5-(5-chloro-2-oxo-1h-pyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2[C@H](C=3C=CC(=CC=3)C#N)N(C=3C(NC=C(Cl)C=3)=O)C(=O)C2=N1 VFMRTUQQYDQOGC-QHCPKHFHSA-N 0.000 claims description 2
YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 claims description 2
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VCGVUTSFODIAFH-UHFFFAOYSA-N 4-[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-3-methylbenzonitrile Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C1=CC=C(C#N)C=C1C VCGVUTSFODIAFH-UHFFFAOYSA-N 0.000 claims description 2
PHONKNJXSTWJFY-UHFFFAOYSA-N 4-[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]benzamide Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C1=CC=C(C(N)=O)C=C1 PHONKNJXSTWJFY-UHFFFAOYSA-N 0.000 claims description 2
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UZPGACSHACEKSI-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]-2-fluorobenzonitrile Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(C#N)=CC=3)N(C=3C(N(C)C=C(Cl)C=3)=O)C(=O)C2=N1 UZPGACSHACEKSI-UHFFFAOYSA-N 0.000 claims description 2
QCBBDTOZLNYFGQ-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]-2-fluorobenzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(C#N)=CC=3)N(C=3C(N(C)C=C(Cl)C=3)=O)C(=O)C2=N1 QCBBDTOZLNYFGQ-UHFFFAOYSA-N 0.000 claims description 2
QFACTYPVKZDPLP-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(=CC=3)C#N)N(C=3C(N(C)C=C(Cl)C=3)=O)C(=O)C2=N1 QFACTYPVKZDPLP-UHFFFAOYSA-N 0.000 claims description 2
IOZOLCKZPLYLKQ-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(=CC=3)C#N)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 IOZOLCKZPLYLKQ-UHFFFAOYSA-N 0.000 claims description 2
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UNRJWGHNUAOTHP-UHFFFAOYSA-N 4-[5-(5-chloro-2-methylphenyl)-2-(5-cyano-2-methoxyphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]-3-methylbenzonitrile Chemical compound COC1=CC=C(C#N)C=C1N1C(C(C)C)=C2C(C=3C(=CC(=CC=3)C#N)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 UNRJWGHNUAOTHP-UHFFFAOYSA-N 0.000 claims description 2
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UBDXCWOLGCQOJC-UHFFFAOYSA-N 4-[5-(5-chloro-2-oxo-1h-pyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]-2-fluorobenzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(C#N)=CC=3)N(C=3C(NC=C(Cl)C=3)=O)C(=O)C2=N1 UBDXCWOLGCQOJC-UHFFFAOYSA-N 0.000 claims description 2
VFMRTUQQYDQOGC-UHFFFAOYSA-N 4-[5-(5-chloro-2-oxo-1h-pyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(=CC=3)C#N)N(C=3C(NC=C(Cl)C=3)=O)C(=O)C2=N1 VFMRTUQQYDQOGC-UHFFFAOYSA-N 0.000 claims description 2
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NIQDSHQHXGATPM-UHFFFAOYSA-N 4-[5-(5-chloro-6-oxo-1h-pyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]-2-fluorobenzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(C#N)=CC=3)N(C=3C=C(Cl)C(=O)NC=3)C(=O)C2=N1 NIQDSHQHXGATPM-UHFFFAOYSA-N 0.000 claims description 2
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CILSJFJSUMUUSU-UHFFFAOYSA-N 4-[[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]methyl]-4-hydroxy-n-propan-2-ylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)NC(C)C)CCC1(O)CN1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 CILSJFJSUMUUSU-UHFFFAOYSA-N 0.000 claims description 2
PSBHMQFAIJWIBA-UHFFFAOYSA-N 4-[[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]methyl]-n-propan-2-ylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)NC(C)C)CCC1CN1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 PSBHMQFAIJWIBA-UHFFFAOYSA-N 0.000 claims description 2
ZFDXOFADVLDFOH-UHFFFAOYSA-N 4-[[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]methyl]-1h-quinolin-2-one Chemical compound O=C1C2=NN(CC=3C4=CC=CC=C4NC(=O)C=3)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC=CC(Cl)=C1F ZFDXOFADVLDFOH-UHFFFAOYSA-N 0.000 claims description 2
KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 claims description 2
DDNUWIGTTWWNTD-UHFFFAOYSA-N 5-(2-chloro-5-methoxypyridin-4-yl)-4-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CN=C(Cl)C=3)OC)C(=O)C2=N1 DDNUWIGTTWWNTD-UHFFFAOYSA-N 0.000 claims description 2
WOGRNEPYKNYRAY-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(2,4-dichlorophenyl)-2-(2-hydroxyethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound O=C1C2=NN(CCO)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)Cl)N1C1=CC=CC(Cl)=C1F WOGRNEPYKNYRAY-UHFFFAOYSA-N 0.000 claims description 2
FOESSPNKSMUVQU-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(3,4-difluorophenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(F)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=N1 FOESSPNKSMUVQU-UHFFFAOYSA-N 0.000 claims description 2
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WMPSGRIFZXRFEB-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(2-hydroxy-2-methylpropyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound O=C1C2=NN(CC(C)(C)O)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC=CC(Cl)=C1F WMPSGRIFZXRFEB-UHFFFAOYSA-N 0.000 claims description 2
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UZHVOERTZALWJN-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chlorophenyl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 UZHVOERTZALWJN-UHFFFAOYSA-N 0.000 claims description 2
JFMPRDLNBMLXEF-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chlorophenyl)-2-[4-methoxy-2-(methylamino)pyrimidin-5-yl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(NC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 JFMPRDLNBMLXEF-UHFFFAOYSA-N 0.000 claims description 2
VJIXYTFQQQTOIG-UHFFFAOYSA-N 5-(5-chloro-2,4-difluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC(F)=C(Cl)C=3)F)C(=O)C2=N1 VJIXYTFQQQTOIG-UHFFFAOYSA-N 0.000 claims description 2
LQBNBLSVDLZZMI-UHFFFAOYSA-N 5-(5-chloro-2-methylphenyl)-4-(5-chloropyridin-2-yl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3N=CC(Cl)=CC=3)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 LQBNBLSVDLZZMI-UHFFFAOYSA-N 0.000 claims description 2
LKJGYPXCEQDHSF-UHFFFAOYSA-N 5-(5-chloro-6-oxo-1h-pyridin-3-yl)-4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C=C(Cl)C(=O)NC=3)C(=O)C2=N1 LKJGYPXCEQDHSF-UHFFFAOYSA-N 0.000 claims description 2
YPYQBKQPNRSJLU-UHFFFAOYSA-N 5-[5-chloro-1-(2-hydroxyethyl)-6-oxopyridin-3-yl]-4-(4-chlorophenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C3=CN(CCO)C(=O)C(Cl)=C3)C(=O)C2=N1 YPYQBKQPNRSJLU-UHFFFAOYSA-N 0.000 claims description 2
IFRLFSYFJZFISV-UHFFFAOYSA-N 5-[5-chloro-1-[2-(dimethylamino)ethyl]-6-oxopyridin-3-yl]-4-(4-chlorophenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C3=CN(CCN(C)C)C(=O)C(Cl)=C3)C(=O)C2=N1 IFRLFSYFJZFISV-UHFFFAOYSA-N 0.000 claims description 2
YBMQYNARIZUNIO-UHFFFAOYSA-N 5-[5-chloro-2-[2-(dimethylamino)ethoxy]phenyl]-4-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)OCCN(C)C)C(=O)C2=N1 YBMQYNARIZUNIO-UHFFFAOYSA-N 0.000 claims description 2
ZYJZAJSSCZJWTL-UHFFFAOYSA-N 5-[5-chloro-2-[2-(dimethylamino)ethoxy]phenyl]-4-(4-chloro-2-methylphenyl)-2-ethyl-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound C12=C(C(C)C)N(CC)N=C2C(=O)N(C=2C(=CC=C(Cl)C=2)OCCN(C)C)C1C1=CC=C(Cl)C=C1C ZYJZAJSSCZJWTL-UHFFFAOYSA-N 0.000 claims description 2
KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 claims description 2
HAOXNUGBZDFVPB-UHFFFAOYSA-N 6-[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-1,3-dimethylpyrimidine-2,4-dione Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1C1=CC(=O)N(C)C(=O)N1C HAOXNUGBZDFVPB-UHFFFAOYSA-N 0.000 claims description 2
VDJFQUDOTQDXAB-UHFFFAOYSA-N 7-[[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4H-pyrrolo[3,4-c]pyrazol-2-yl]methyl]-5-oxo-4H-pyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound CC(C)c1c2C(N(C(=O)c2nn1Cc1cc(=O)[nH]c2c(cnn12)C#N)c1cccc(Cl)c1F)c1ccc(Cl)cc1C VDJFQUDOTQDXAB-UHFFFAOYSA-N 0.000 claims description 2
CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 claims description 2
GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 claims description 2
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 claims description 2
LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 claims description 2
239000013543 active substance Substances 0.000 claims description 2
125000002619 bicyclic group Chemical group 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
KACZQOKEFKFNDB-UHFFFAOYSA-N ethyl 1h-pyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NNC=1 KACZQOKEFKFNDB-UHFFFAOYSA-N 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
UDHRMOWCYWTZJA-LWAJAQLZSA-N methyl (2s)-2-[[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]methyl]pyrrolidine-1-carboxylate Chemical compound COC(=O)N1CCC[C@H]1CN1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 UDHRMOWCYWTZJA-LWAJAQLZSA-N 0.000 claims description 2
OATMHJTYDZFHJL-UHFFFAOYSA-N methyl 3-[5-(3-chloro-4-fluorophenyl)-4-(4-chlorophenyl)-2-(2-methoxyphenyl)-6-oxo-3-propan-2-ylpyrrolo[3,4-c]pyrazol-4-yl]propanoate Chemical compound CC(C)C1=C2C(CCC(=O)OC)(C=3C=CC(Cl)=CC=3)N(C=3C=C(Cl)C(F)=CC=3)C(=O)C2=NN1C1=CC=CC=C1OC OATMHJTYDZFHJL-UHFFFAOYSA-N 0.000 claims description 2
PYHGZMRCOVTXPO-UHFFFAOYSA-N n-[2-[5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-4h-pyrrolo[3,4-c]pyrazol-3-yl]propyl]acetamide Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)CNC(C)=O)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=N1 PYHGZMRCOVTXPO-UHFFFAOYSA-N 0.000 claims description 2
IMRHOXBGCDZUNF-UHFFFAOYSA-N n-[2-[5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-4h-pyrrolo[3,4-c]pyrazol-3-yl]propyl]formamide Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)CNC=O)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=N1 IMRHOXBGCDZUNF-UHFFFAOYSA-N 0.000 claims description 2
PAUGXEQSQVHHPG-UHFFFAOYSA-N n-[3-chloro-5-[4-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-5-yl]phenyl]acetamide Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C=C(NC(C)=O)C=C(Cl)C=3)C(=O)C2=N1 PAUGXEQSQVHHPG-UHFFFAOYSA-N 0.000 claims description 2
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POEYXKUAFFVQOZ-UHFFFAOYSA-N n-[[3-[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-4-methoxyphenyl]methyl]formamide Chemical compound COC1=CC=C(CNC=O)C=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 POEYXKUAFFVQOZ-UHFFFAOYSA-N 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
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IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
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XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 claims description 2
ODOZCWBAEOCSHE-UHFFFAOYSA-N tert-butyl 3-[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]pyrrolidine-1-carboxylate Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1C1CCN(C(=O)OC(C)(C)C)C1 ODOZCWBAEOCSHE-UHFFFAOYSA-N 0.000 claims description 2
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FWEMNIDYMWXHEJ-UHFFFAOYSA-N 5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-4-(4-chlorophenyl)-2-[4-methoxy-2-(methylamino)pyrimidin-5-yl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(NC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(N(C)C=C(Cl)C=3)=O)C(=O)C2=N1 FWEMNIDYMWXHEJ-UHFFFAOYSA-N 0.000 claims 1
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JP2014544018A 2011-11-29 2012-11-28 ピラゾロピロリジン化合物 Expired - Fee Related JP5992054B2 (ja)