HRP20010742A2 - Pyrazolobenzodiazepines as cdk2 inhibitors - Google Patents

Pyrazolobenzodiazepines as cdk2 inhibitors Download PDF

Info

Publication number: HRP20010742A2
Authority: HR; Croatia
Prior art keywords: benzodiazepine; pyrazolo; chlorophenyl; nitro; methyl
Prior art date: 1999-04-21

Application number

HR20010742A

Other languages

English (en)

Croatian (hr)

Inventor

Qingjie Ding

Jin-Jun Liu

Vincent

Giacomo Pizzolato

Chung-Chen Wei

Peter Michael Wovkulich

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

1999-04-21

Filing date

2001-10-12

Publication date

2002-12-31

2001-10-12 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2002-12-31 Publication of HRP20010742A2 publication Critical patent/HRP20010742A2/hr

Links

QBCJSMSLBBCZGU-UHFFFAOYSA-N pyrazolo[3,4-i][1,2]benzodiazepine Chemical class C1=CN=NC2=C3C=NN=C3C=CC2=C1 QBCJSMSLBBCZGU-UHFFFAOYSA-N 0.000 title description 5
239000003112 inhibitor Substances 0.000 title description 3
101150073031 cdk2 gene Proteins 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 199
125000000217 alkyl group Chemical group 0.000 claims description 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
229910052739 hydrogen Inorganic materials 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 26
229910052736 halogen Inorganic materials 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 19
150000002367 halogens Chemical group 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
239000000651 prodrug Chemical group 0.000 claims description 15
229940002612 prodrug Drugs 0.000 claims description 15
-1 5-(2-chlorophenyl)-7-amino-pyrazolo[3,4][1,4]benzodiazepine 5-phenyl-7-chloro-pyrazolo[3,4][1,4]benzodiazepine Chemical compound 0.000 claims description 14
210000001072 colon Anatomy 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
125000000623 heterocyclic group Chemical group 0.000 claims description 11
210000000481 breast Anatomy 0.000 claims description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
208000026310 Breast neoplasm Diseases 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 8
239000000825 pharmaceutical preparation Substances 0.000 claims description 8
208000029742 colonic neoplasm Diseases 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
239000002207 metabolite Substances 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
150000002431 hydrogen Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000001072 heteroaryl group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
PHTNFRNPQIUWKC-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-cyclopropyl-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C1CC1 PHTNFRNPQIUWKC-UHFFFAOYSA-N 0.000 claims description 3
JJGGQXHWUMXVAS-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-methyl-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical group N=1C(C)=CN=C2C3=CN=NC3=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1Cl JJGGQXHWUMXVAS-UHFFFAOYSA-N 0.000 claims description 3
IZGJNHSAHZFTKD-UHFFFAOYSA-N 7-iodo-3-methyl-5-phenylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(C)=CN=C2C3=CN=NC3=C(I)C=C2C=1C1=CC=CC=C1 IZGJNHSAHZFTKD-UHFFFAOYSA-N 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
208000023958 prostate neoplasm Diseases 0.000 claims description 3
GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims description 2
CGJDUGAFOYIHTB-UHFFFAOYSA-N 1-[5-(2-chlorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepin-3-yl]-n,n-dimethylmethanamine Chemical compound N=1C(CN(C)C)=CN=C2C3=CN=NC3=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1Cl CGJDUGAFOYIHTB-UHFFFAOYSA-N 0.000 claims description 2
XTWNGXKBMHZIER-UHFFFAOYSA-N 3-benzyl-5-(2-chlorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1CC1=CC=CC=C1 XTWNGXKBMHZIER-UHFFFAOYSA-N 0.000 claims description 2
HSFQXDXHXDMILT-UHFFFAOYSA-N 3-butan-2-yl-5-(2-chlorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(C(C)CC)=CN=C2C3=CN=NC3=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1Cl HSFQXDXHXDMILT-UHFFFAOYSA-N 0.000 claims description 2
UHLHKEDGAYUSTO-UHFFFAOYSA-N 3-methyl-7-nitro-5-phenylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(C)=CN=C2C3=CN=NC3=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 UHLHKEDGAYUSTO-UHFFFAOYSA-N 0.000 claims description 2
OFWRSDREYGYKGJ-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(1h-imidazol-5-yl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C1=CNC=N1 OFWRSDREYGYKGJ-UHFFFAOYSA-N 0.000 claims description 2
WNDSNMARKFKCIF-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(2-methylpropyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(CC(C)C)=CN=C2C3=CN=NC3=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1Cl WNDSNMARKFKCIF-UHFFFAOYSA-N 0.000 claims description 2
XULTYYGWUDIBIW-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(methoxymethyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(COC)=CN=C2C3=CN=NC3=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1Cl XULTYYGWUDIBIW-UHFFFAOYSA-N 0.000 claims description 2
KMXPHGKNZQNROX-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-ethenyl-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=C(C=C)C=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C1C1=CC=CC=C1Cl KMXPHGKNZQNROX-UHFFFAOYSA-N 0.000 claims description 2
BGAWSOWJMONNFD-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-ethyl-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(CC)=CN=C2C3=CN=NC3=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1Cl BGAWSOWJMONNFD-UHFFFAOYSA-N 0.000 claims description 2
QPEVVQRRJHXGRY-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-methylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(C)=CN=C2C3=CN=NC3=CC=C2C=1C1=CC=CC=C1Cl QPEVVQRRJHXGRY-UHFFFAOYSA-N 0.000 claims description 2
SFYHCLIBZXPRMU-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-propan-2-ylpyrazolo[3,4-i][1,4]benzodiazepin-7-amine Chemical compound N=1C(C(C)C)=CN=C2C3=CN=NC3=C(N)C=C2C=1C1=CC=CC=C1Cl SFYHCLIBZXPRMU-UHFFFAOYSA-N 0.000 claims description 2
MPKKGHVTTPSQPL-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-methoxypyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=CC=NC2=C3C=NN=C3C(OC)=CC2=C1C1=CC=CC=C1Cl MPKKGHVTTPSQPL-UHFFFAOYSA-N 0.000 claims description 2
KVWPQZLDEBQZSC-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-(1h-pyrazol-5-yl)pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C=1C=CNN=1 KVWPQZLDEBQZSC-UHFFFAOYSA-N 0.000 claims description 2
JWGAEBZTHFZGKM-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-(1h-pyrrol-2-yl)pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C1=CC=CN1 JWGAEBZTHFZGKM-UHFFFAOYSA-N 0.000 claims description 2
HOKRLOYXSZZVKP-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-(2-phenylethyl)pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1CCC1=CC=CC=C1 HOKRLOYXSZZVKP-UHFFFAOYSA-N 0.000 claims description 2
LXVBZQKLBLFLDJ-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-(trifluoromethyl)pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=C(C(F)(F)F)C=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C1C1=CC=CC=C1Cl LXVBZQKLBLFLDJ-UHFFFAOYSA-N 0.000 claims description 2
HPJMNQBJIUWWHZ-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-phenylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC=C1 HPJMNQBJIUWWHZ-UHFFFAOYSA-N 0.000 claims description 2
WYVODKLLIDDJIN-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-propan-2-ylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(C(C)C)=CN=C2C3=CN=NC3=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1Cl WYVODKLLIDDJIN-UHFFFAOYSA-N 0.000 claims description 2
PGYWEBOUEIOXHG-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-propylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(CCC)=CN=C2C3=CN=NC3=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1Cl PGYWEBOUEIOXHG-UHFFFAOYSA-N 0.000 claims description 2
GTNNJCPSLJCCLP-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-pyrazol-1-ylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1N1C=CC=N1 GTNNJCPSLJCCLP-UHFFFAOYSA-N 0.000 claims description 2
JSOYSJVRPOLDIB-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=CC=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C1C1=CC=CC=C1Cl JSOYSJVRPOLDIB-UHFFFAOYSA-N 0.000 claims description 2
AMPXSKXWAJDCAY-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine-3-carbaldehyde Chemical compound N1=C(C=O)C=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C1C1=CC=CC=C1Cl AMPXSKXWAJDCAY-UHFFFAOYSA-N 0.000 claims description 2
FSHHPYCWHJMLSC-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine-3-carbonitrile Chemical compound N1=C(C#N)C=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C1C1=CC=CC=C1Cl FSHHPYCWHJMLSC-UHFFFAOYSA-N 0.000 claims description 2
HPDUBBCFARSERL-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine-3-carboxamide Chemical compound N=1C(C(=O)N)=CN=C2C3=CN=NC3=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1Cl HPDUBBCFARSERL-UHFFFAOYSA-N 0.000 claims description 2
CQCCAQYYDLMFBY-UHFFFAOYSA-N 5-(2-fluorophenyl)-3-(hydroxymethyl)pyrazolo[3,4-i][1,4]benzodiazepine-7-carbonitrile Chemical group N=1C(CO)=CN=C2C3=CN=NC3=C(C#N)C=C2C=1C1=CC=CC=C1F CQCCAQYYDLMFBY-UHFFFAOYSA-N 0.000 claims description 2
DCCPWWJJFVJDKB-UHFFFAOYSA-N 5-(2-fluorophenyl)-3-methyl-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(C)=CN=C2C3=CN=NC3=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F DCCPWWJJFVJDKB-UHFFFAOYSA-N 0.000 claims description 2
YQGSZJOIADOUQX-UHFFFAOYSA-N 5-(2-fluorophenyl)-3-methylpyrazolo[3,4-i][1,4]benzodiazepine-7-carbonitrile Chemical group N=1C(C)=CN=C2C3=CN=NC3=C(C#N)C=C2C=1C1=CC=CC=C1F YQGSZJOIADOUQX-UHFFFAOYSA-N 0.000 claims description 2
ZHAYIETWSBKSID-UHFFFAOYSA-N 5-(2-fluorophenyl)-3-methylpyrazolo[3,4-i][1,4]benzodiazepine-7-carboxamide Chemical group N=1C(C)=CN=C2C3=CN=NC3=C(C(N)=O)C=C2C=1C1=CC=CC=C1F ZHAYIETWSBKSID-UHFFFAOYSA-N 0.000 claims description 2
ZOYUTSBNHKSWFH-UHFFFAOYSA-N 5-(2-fluorophenyl)-7-iodo-3-methylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(C)=CN=C2C3=CN=NC3=C(I)C=C2C=1C1=CC=CC=C1F ZOYUTSBNHKSWFH-UHFFFAOYSA-N 0.000 claims description 2
DSCKBFOEVNZHSD-UHFFFAOYSA-N 5-(2-fluorophenyl)-7-iodopyrazolo[3,4-i][1,4]benzodiazepine Chemical compound FC1=CC=CC=C1C1=NC=CN=C2C1=CC(I)=C1N=NC=C12 DSCKBFOEVNZHSD-UHFFFAOYSA-N 0.000 claims description 2
YMWYFETZSIACMI-UHFFFAOYSA-N 5-(2-fluorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=CC=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C1C1=CC=CC=C1F YMWYFETZSIACMI-UHFFFAOYSA-N 0.000 claims description 2
BINAVSWISHYZAV-UHFFFAOYSA-N 5-(2-fluorophenyl)-n,n-bis(2-hydroxyethyl)pyrazolo[3,4-i][1,4]benzodiazepine-7-carboxamide Chemical compound N1=CC=NC2=C3C=NN=C3C(C(=O)N(CCO)CCO)=CC2=C1C1=CC=CC=C1F BINAVSWISHYZAV-UHFFFAOYSA-N 0.000 claims description 2
GFKQOJBRLPAZIM-UHFFFAOYSA-N 5-(2-fluorophenyl)-n-(2-hydroxyethyl)pyrazolo[3,4-i][1,4]benzodiazepine-7-carboxamide Chemical compound N1=CC=NC2=C3C=NN=C3C(C(=O)NCCO)=CC2=C1C1=CC=CC=C1F GFKQOJBRLPAZIM-UHFFFAOYSA-N 0.000 claims description 2
XTHFLXPPCJCRCV-UHFFFAOYSA-N 5-(2-fluorophenyl)pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound FC1=CC=CC=C1C1=NC=CN=C2C1=CC=C1N=NC=C12 XTHFLXPPCJCRCV-UHFFFAOYSA-N 0.000 claims description 2
NKKYOHGUIFRIGR-UHFFFAOYSA-N 5-(2-fluorophenyl)pyrazolo[3,4-i][1,4]benzodiazepine-7-carbonitrile Chemical compound FC1=CC=CC=C1C1=NC=CN=C2C1=CC(C#N)=C1N=NC=C12 NKKYOHGUIFRIGR-UHFFFAOYSA-N 0.000 claims description 2
ANSFKHHLWMGXOS-UHFFFAOYSA-N 5-phenylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=CC=NC2=C3C=NN=C3C=CC2=C1C1=CC=CC=C1 ANSFKHHLWMGXOS-UHFFFAOYSA-N 0.000 claims description 2
VDFDWUJTYQVVKI-UHFFFAOYSA-N 7-bromo-3-methyl-5-phenylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(C)=CN=C2C3=CN=NC3=C(Br)C=C2C=1C1=CC=CC=C1 VDFDWUJTYQVVKI-UHFFFAOYSA-N 0.000 claims description 2
MKDASOXGVVGWEJ-UHFFFAOYSA-N 7-chloro-5-(2,4-dichlorophenyl)pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound ClC1=CC(Cl)=CC=C1C1=NC=CN=C2C1=CC(Cl)=C1N=NC=C12 MKDASOXGVVGWEJ-UHFFFAOYSA-N 0.000 claims description 2
NRIUOAGROAIQFX-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-3-methylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(C)=CN=C2C3=CN=NC3=C(Cl)C=C2C=1C1=CC=CC=C1Cl NRIUOAGROAIQFX-UHFFFAOYSA-N 0.000 claims description 2
ZHWNRINMEYNKEO-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound ClC1=CC=CC=C1C1=NC=CN=C2C1=CC(Cl)=C1N=NC=C12 ZHWNRINMEYNKEO-UHFFFAOYSA-N 0.000 claims description 2
VIRZTGGBXATKRK-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-3-methylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(C)=CN=C2C3=CN=NC3=C(Cl)C=C2C=1C1=CC=CC=C1F VIRZTGGBXATKRK-UHFFFAOYSA-N 0.000 claims description 2
HQYMNMKHMKIDEA-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound FC1=CC=CC=C1C1=NC=CN=C2C1=CC(Cl)=C1N=NC=C12 HQYMNMKHMKIDEA-UHFFFAOYSA-N 0.000 claims description 2
YYNADVCNWNNESS-UHFFFAOYSA-N 7-fluoro-3-methyl-5-phenylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(C)=CN=C2C3=CN=NC3=C(F)C=C2C=1C1=CC=CC=C1 YYNADVCNWNNESS-UHFFFAOYSA-N 0.000 claims description 2
HNNKBZNZOZXPSW-UHFFFAOYSA-N 7-fluoro-5-(2-fluorophenyl)-3-methylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(C)=CN=C2C3=CN=NC3=C(F)C=C2C=1C1=CC=CC=C1F HNNKBZNZOZXPSW-UHFFFAOYSA-N 0.000 claims description 2
SAYYEHPNKHRUPG-UHFFFAOYSA-N 7-fluoro-5-(2-fluorophenyl)pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound FC1=CC=CC=C1C1=NC=CN=C2C1=CC(F)=C1N=NC=C12 SAYYEHPNKHRUPG-UHFFFAOYSA-N 0.000 claims description 2
CQKGSXJJMDROBJ-UHFFFAOYSA-N 7-methylsulfonyl-5-phenylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=CC=NC2=C3C=NN=C3C(S(=O)(=O)C)=CC2=C1C1=CC=CC=C1 CQKGSXJJMDROBJ-UHFFFAOYSA-N 0.000 claims description 2
JOVGYUXQTZHZEA-UHFFFAOYSA-N 7-nitro-5-[2-(trifluoromethyl)phenyl]pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=CC=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C1C1=CC=CC=C1C(F)(F)F JOVGYUXQTZHZEA-UHFFFAOYSA-N 0.000 claims description 2
VYCSQLMGSOJUFC-UHFFFAOYSA-N 7-nitro-5-phenylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=CC=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C1C1=CC=CC=C1 VYCSQLMGSOJUFC-UHFFFAOYSA-N 0.000 claims description 2
QGGINYQQBSKSKP-UHFFFAOYSA-N CC1=CN=C2C(=CC(=C3C2=CN=N3)N)C(=N1)C4=CC=CC=C4F Chemical compound CC1=CN=C2C(=CC(=C3C2=CN=N3)N)C(=N1)C4=CC=CC=C4F QGGINYQQBSKSKP-UHFFFAOYSA-N 0.000 claims description 2
XEXRYRHHVLPJOB-UHFFFAOYSA-N FC1=C(C=CC=C1)C=1N=CC=NC=2C=1C=C(C=1C=2C=NN=1)C(=O)N1CCOCC1 Chemical compound FC1=C(C=CC=C1)C=1N=CC=NC=2C=1C=C(C=1C=2C=NN=1)C(=O)N1CCOCC1 XEXRYRHHVLPJOB-UHFFFAOYSA-N 0.000 claims description 2
UKCJZRZZXIYXEW-UHFFFAOYSA-N [5-(2-chlorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepin-3-yl]methanol Chemical compound N=1C(CO)=CN=C2C3=CN=NC3=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1Cl UKCJZRZZXIYXEW-UHFFFAOYSA-N 0.000 claims description 2
IVPBZCJMGMVVGV-UHFFFAOYSA-N [O-][N+](C(C1=NN=CC1=C1N=C2)=CC1=C(C1=CC=CC=C1Cl)N=C2[S+]1C=NC=C1)=O Chemical compound [O-][N+](C(C1=NN=CC1=C1N=C2)=CC1=C(C1=CC=CC=C1Cl)N=C2[S+]1C=NC=C1)=O IVPBZCJMGMVVGV-UHFFFAOYSA-N 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
WJSCPXNAFJEGED-UHFFFAOYSA-N ethyl 5-(2-chlorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine-3-carboxylate Chemical compound N=1C(C(=O)OCC)=CN=C2C3=CN=NC3=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1Cl WJSCPXNAFJEGED-UHFFFAOYSA-N 0.000 claims description 2
ANPLFLPGJGCDIN-UHFFFAOYSA-N ethyl 5-(2-fluorophenyl)-3-methylpyrazolo[3,4-i][1,4]benzodiazepine-7-carboxylate Chemical compound N1=C(C)C=NC2=C3C=NN=C3C(C(=O)OCC)=CC2=C1C1=CC=CC=C1F ANPLFLPGJGCDIN-UHFFFAOYSA-N 0.000 claims description 2
KXODDHVDMALSCS-UHFFFAOYSA-N ethyl 5-(2-fluorophenyl)pyrazolo[3,4-i][1,4]benzodiazepine-7-carboxylate Chemical compound N1=CC=NC2=C3C=NN=C3C(C(=O)OCC)=CC2=C1C1=CC=CC=C1F KXODDHVDMALSCS-UHFFFAOYSA-N 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
210000004072 lung Anatomy 0.000 claims description 2
208000037841 lung tumor Diseases 0.000 claims description 2
XWEMZPHHOWKDKZ-UHFFFAOYSA-N n-[5-(2-chlorophenyl)-3-methylpyrazolo[3,4-i][1,4]benzodiazepin-7-yl]acetamide Chemical compound N1=C(C)C=NC2=C3C=NN=C3C(NC(=O)C)=CC2=C1C1=CC=CC=C1Cl XWEMZPHHOWKDKZ-UHFFFAOYSA-N 0.000 claims description 2
AKZGBBLFKXQLMK-UHFFFAOYSA-N n-[5-(2-chlorophenyl)-3-methylpyrazolo[3,4-i][1,4]benzodiazepin-7-yl]methanesulfonamide Chemical compound N=1C(C)=CN=C2C3=CN=NC3=C(NS(C)(=O)=O)C=C2C=1C1=CC=CC=C1Cl AKZGBBLFKXQLMK-UHFFFAOYSA-N 0.000 claims description 2
QMKPHPUECBUDLK-UHFFFAOYSA-N n-[5-(2-chlorophenyl)-3-methylpyrazolo[3,4-i][1,4]benzodiazepin-7-yl]prop-2-enamide Chemical compound N=1C(C)=CN=C2C3=CN=NC3=C(NC(=O)C=C)C=C2C=1C1=CC=CC=C1Cl QMKPHPUECBUDLK-UHFFFAOYSA-N 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
MVEPZYUIHJYSMW-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(3-methylthiophen-2-yl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=CSC(C=2N=C(C3=CC(=C4N=NC=C4C3=NC=2)[N+]([O-])=O)C=2C(=CC=CC=2)Cl)=C1C MVEPZYUIHJYSMW-UHFFFAOYSA-N 0.000 claims 2
VZCCDYLFAHYQAF-UHFFFAOYSA-N 2-[5-(2-chlorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepin-3-yl]-1,3,4-oxadiazole Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C1=NN=CO1 VZCCDYLFAHYQAF-UHFFFAOYSA-N 0.000 claims 1
ICVQNHARRHAQOE-UHFFFAOYSA-N 3-(1,3-benzodioxol-4-yl)-5-(2-chlorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=C(C=2C=3OCOC=3C=CC=2)C=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C1C1=CC=CC=C1Cl ICVQNHARRHAQOE-UHFFFAOYSA-N 0.000 claims 1
RIRZYXPHINXCOM-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-7-nitro-5-phenylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=C(C=2C=C3OCOC3=CC=2)C=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C1C1=CC=CC=C1 RIRZYXPHINXCOM-UHFFFAOYSA-N 0.000 claims 1
GIEFOQKSVMHIQL-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)-5-(2-chlorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=C(C=2OC3=CC=CC=C3C=2)C=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C1C1=CC=CC=C1Cl GIEFOQKSVMHIQL-UHFFFAOYSA-N 0.000 claims 1
FNKKKRDENFXAQL-UHFFFAOYSA-N 3-(1h-imidazol-2-yl)-7-nitro-5-phenylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C=CC=CC=2)N=C1C1=NC=CN1 FNKKKRDENFXAQL-UHFFFAOYSA-N 0.000 claims 1
KIIGCLAYQHXZPJ-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-7-nitro-5-phenylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=C(C=2C=C3OCCOC3=CC=2)C=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C1C1=CC=CC=C1 KIIGCLAYQHXZPJ-UHFFFAOYSA-N 0.000 claims 1
KBYINRVXHADDMT-UHFFFAOYSA-N 3-(2-fluorophenyl)-7-nitro-5-phenylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1F KBYINRVXHADDMT-UHFFFAOYSA-N 0.000 claims 1
DINAOBBIPLTIBN-UHFFFAOYSA-N 3-[5-(2-chlorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepin-3-yl]benzonitrile Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC(C#N)=C1 DINAOBBIPLTIBN-UHFFFAOYSA-N 0.000 claims 1
JGHZJMOPZRXDGF-UHFFFAOYSA-N 3-[5-(2-chlorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepin-3-yl]phenol Chemical compound OC1=CC=CC(C=2N=C(C3=CC(=C4N=NC=C4C3=NC=2)[N+]([O-])=O)C=2C(=CC=CC=2)Cl)=C1 JGHZJMOPZRXDGF-UHFFFAOYSA-N 0.000 claims 1
NURIIOVTNJAXLQ-UHFFFAOYSA-N 3-methyl-7-nitro-5-[2-(trifluoromethyl)phenyl]pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N=1C(C)=CN=C2C3=CN=NC3=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1C(F)(F)F NURIIOVTNJAXLQ-UHFFFAOYSA-N 0.000 claims 1
VOEKILCSLOBEAB-UHFFFAOYSA-N 4-[5-(2-chlorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepin-3-yl]-3-methoxyphenol Chemical compound COC1=CC(O)=CC=C1C(N=C1C=2C(=CC=CC=2)Cl)=CN=C2C1=CC([N+]([O-])=O)=C1N=NC=C12 VOEKILCSLOBEAB-UHFFFAOYSA-N 0.000 claims 1
JYKIUXYXBVMEPF-UHFFFAOYSA-N 4-[5-(2-chlorophenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepin-3-yl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(N=C1C=2C(=CC=CC=2)Cl)=CN=C2C1=CC([N+]([O-])=O)=C1N=NC=C12 JYKIUXYXBVMEPF-UHFFFAOYSA-N 0.000 claims 1
DQPKSVLXYWOYNW-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(1-methylpyrrol-2-yl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound CN1C=CC=C1C(N=C1C=2C(=CC=CC=2)Cl)=CN=C2C1=CC([N+]([O-])=O)=C1N=NC=C12 DQPKSVLXYWOYNW-UHFFFAOYSA-N 0.000 claims 1
BMVFHNFSSZDRCQ-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(1h-indol-2-yl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=C(C=2NC3=CC=CC=C3C=2)C=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C1C1=CC=CC=C1Cl BMVFHNFSSZDRCQ-UHFFFAOYSA-N 0.000 claims 1
JPCGYGXAXKUMCD-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(2-methoxyphenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound COC1=CC=CC=C1C(N=C1C=2C(=CC=CC=2)Cl)=CN=C2C1=CC([N+]([O-])=O)=C1N=NC=C12 JPCGYGXAXKUMCD-UHFFFAOYSA-N 0.000 claims 1
HCTJMUMYZIDNLZ-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(2-methylphenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound CC1=CC=CC=C1C(N=C1C=2C(=CC=CC=2)Cl)=CN=C2C1=CC([N+]([O-])=O)=C1N=NC=C12 HCTJMUMYZIDNLZ-UHFFFAOYSA-N 0.000 claims 1
JWWVLWGQUVIOLZ-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(3-ethoxyphenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound CCOC1=CC=CC(C=2N=C(C3=CC(=C4N=NC=C4C3=NC=2)[N+]([O-])=O)C=2C(=CC=CC=2)Cl)=C1 JWWVLWGQUVIOLZ-UHFFFAOYSA-N 0.000 claims 1
FRXPRIPUDHUPLZ-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(3-methylphenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound CC1=CC=CC(C=2N=C(C3=CC(=C4N=NC=C4C3=NC=2)[N+]([O-])=O)C=2C(=CC=CC=2)Cl)=C1 FRXPRIPUDHUPLZ-UHFFFAOYSA-N 0.000 claims 1
FRIJFPNCUIZWGR-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(4-methyl-1h-pyrazol-5-yl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NNC(C=2N=C(C3=CC(=C4N=NC=C4C3=NC=2)[N+]([O-])=O)C=2C(=CC=CC=2)Cl)=C1C FRIJFPNCUIZWGR-UHFFFAOYSA-N 0.000 claims 1
KRFYMJLBHVIHKH-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(4-methylphenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=CC(C)=CC=C1C(N=C1C=2C(=CC=CC=2)Cl)=CN=C2C1=CC([N+]([O-])=O)=C1N=NC=C12 KRFYMJLBHVIHKH-UHFFFAOYSA-N 0.000 claims 1
MAPJDNCIAKCMJZ-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(4-methylsulfanylphenyl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=CC(SC)=CC=C1C(N=C1C=2C(=CC=CC=2)Cl)=CN=C2C1=CC([N+]([O-])=O)=C1N=NC=C12 MAPJDNCIAKCMJZ-UHFFFAOYSA-N 0.000 claims 1
PCRZEOYLBAQPRJ-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(5-methylthiophen-2-yl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound S1C(C)=CC=C1C(N=C1C=2C(=CC=CC=2)Cl)=CN=C2C1=CC([N+]([O-])=O)=C1N=NC=C12 PCRZEOYLBAQPRJ-UHFFFAOYSA-N 0.000 claims 1
OJRMNYPHVBYVOI-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(furan-2-yl)-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C1=CC=CO1 OJRMNYPHVBYVOI-UHFFFAOYSA-N 0.000 claims 1
AOGAFBFOFOSCBR-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-isoquinolin-4-yl-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=C(C=2C3=CC=CC=C3C=NC=2)C=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C1C1=CC=CC=C1Cl AOGAFBFOFOSCBR-UHFFFAOYSA-N 0.000 claims 1
QCTBCAMPRRMFKO-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-naphthalen-1-yl-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=C(C=2C3=CC=CC=C3C=CC=2)C=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C1C1=CC=CC=C1Cl QCTBCAMPRRMFKO-UHFFFAOYSA-N 0.000 claims 1
IQZKWLFDJBODGZ-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-naphthalen-2-yl-7-nitropyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=C(C=2C=C3C=CC=CC3=CC=2)C=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C1C1=CC=CC=C1Cl IQZKWLFDJBODGZ-UHFFFAOYSA-N 0.000 claims 1
BSDXWBPMASBQAU-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-methoxy-3-methylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound N1=C(C)C=NC2=C3C=NN=C3C(OC)=CC2=C1C1=CC=CC=C1Cl BSDXWBPMASBQAU-UHFFFAOYSA-N 0.000 claims 1
NVTMZZLJSKMUQN-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-(2-nitrophenyl)pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound [O-][N+](=O)C1=CC=CC=C1C(N=C1C=2C(=CC=CC=2)Cl)=CN=C2C1=CC([N+]([O-])=O)=C1N=NC=C12 NVTMZZLJSKMUQN-UHFFFAOYSA-N 0.000 claims 1
ASPCYUZHKUZICQ-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-(3-nitrophenyl)pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(C3=CC(=C4N=NC=C4C3=NC=2)[N+]([O-])=O)C=2C(=CC=CC=2)Cl)=C1 ASPCYUZHKUZICQ-UHFFFAOYSA-N 0.000 claims 1
RCRSEFQIDGDDKG-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-(3-phenoxyphenyl)pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C(C=1)=CC=CC=1OC1=CC=CC=C1 RCRSEFQIDGDDKG-UHFFFAOYSA-N 0.000 claims 1
IUEZHFXCSSATIA-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-(4-phenylphenyl)pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C(C=C1)=CC=C1C1=CC=CC=C1 IUEZHFXCSSATIA-UHFFFAOYSA-N 0.000 claims 1
HGIGZOSOQGKPJL-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-(4-pyrrol-1-ylphenyl)pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C(C=C1)=CC=C1N1C=CC=C1 HGIGZOSOQGKPJL-UHFFFAOYSA-N 0.000 claims 1
HEQNZNVZPQTEJY-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-[2-(trifluoromethyl)phenyl]pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC=C1C(F)(F)F HEQNZNVZPQTEJY-UHFFFAOYSA-N 0.000 claims 1
FDNUGGHVLPCYAQ-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-[3-(trifluoromethyl)phenyl]pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC(C(F)(F)F)=C1 FDNUGGHVLPCYAQ-UHFFFAOYSA-N 0.000 claims 1
BRQARBMTDIFBGK-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C1=CC=C(OC(F)(F)F)C=C1 BRQARBMTDIFBGK-UHFFFAOYSA-N 0.000 claims 1
ANFUWBAMIUUALL-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-pyridin-3-ylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C1=CC=CN=C1 ANFUWBAMIUUALL-UHFFFAOYSA-N 0.000 claims 1
IRJNSEHYRMWRIU-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-pyridin-4-ylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C1=CC=NC=C1 IRJNSEHYRMWRIU-UHFFFAOYSA-N 0.000 claims 1
HWZXQFWEFMQWDG-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-thiophen-2-ylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C1=CC=CS1 HWZXQFWEFMQWDG-UHFFFAOYSA-N 0.000 claims 1
DUEURXOSMNKJAI-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-3-thiophen-3-ylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C(=CC=CC=2)Cl)N=C1C=1C=CSC=1 DUEURXOSMNKJAI-UHFFFAOYSA-N 0.000 claims 1
RGXQYCQGQZQVRL-UHFFFAOYSA-N 5-(2-fluorophenyl)-3-methyl-n-(2-morpholin-4-ylethyl)pyrazolo[3,4-i][1,4]benzodiazepine-7-carboxamide Chemical compound N=1C(C)=CN=C2C3=CN=NC3=C(C(=O)NCCN3CCOCC3)C=C2C=1C1=CC=CC=C1F RGXQYCQGQZQVRL-UHFFFAOYSA-N 0.000 claims 1
GAYNKMRXNWSUMW-UHFFFAOYSA-N 5-(2-fluorophenyl)pyrazolo[3,4-i][1,4]benzodiazepine-7-carboxamide Chemical compound N1=CC=NC2=C3C=NN=C3C(C(=O)N)=CC2=C1C1=CC=CC=C1F GAYNKMRXNWSUMW-UHFFFAOYSA-N 0.000 claims 1
PCVGQAVBXYUNOI-UHFFFAOYSA-N 5-(2-fluorophenyl)pyrazolo[3,4-i][1,4]benzodiazepine-7-carboxylic acid Chemical compound N1=CC=NC2=C3C=NN=C3C(C(=O)O)=CC2=C1C1=CC=CC=C1F PCVGQAVBXYUNOI-UHFFFAOYSA-N 0.000 claims 1
LEZSLBLUVOKISX-UHFFFAOYSA-N 7-nitro-5-(3-nitrophenyl)pyrazolo[3,4-i][1,4]benzodiazepine Chemical compound [O-][N+](=O)C1=CC=CC(C=2C3=CC(=C4N=NC=C4C3=NC=CN=2)[N+]([O-])=O)=C1 LEZSLBLUVOKISX-UHFFFAOYSA-N 0.000 claims 1
KHWBQLMRQSYCFA-UHFFFAOYSA-N 7-nitro-5-phenyl-3-pyridin-3-ylpyrazolo[3,4-i][1,4]benzodiazepine Chemical compound C1=NC2=C3C=NN=C3C([N+](=O)[O-])=CC2=C(C=2C=CC=CC=2)N=C1C1=CC=CN=C1 KHWBQLMRQSYCFA-UHFFFAOYSA-N 0.000 claims 1
WFKBKVTUSCJAGK-UHFFFAOYSA-N CC=1C=NC=2C(=C(N=1)C1=C(C=CC=C1)F)C=C(C=1C=2C=NN=1)C(=O)N1CCOCC1 Chemical compound CC=1C=NC=2C(=C(N=1)C1=C(C=CC=C1)F)C=C(C=1C=2C=NN=1)C(=O)N1CCOCC1 WFKBKVTUSCJAGK-UHFFFAOYSA-N 0.000 claims 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/22—Sulfur atoms

HR20010742A 1999-04-21 2001-10-12 Pyrazolobenzodiazepines as cdk2 inhibitors HRP20010742A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US13037099P	1999-04-21	1999-04-21
PCT/EP2000/003394 WO2000064900A1 (en)	1999-04-21	2000-04-14	Pyrazolobenzodiazepines as cdk2 inhibitors

Publications (1)

Publication Number	Publication Date
HRP20010742A2 true HRP20010742A2 (en)	2002-12-31

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ID=22444382

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HR20010742A HRP20010742A2 (en)	1999-04-21	2001-10-12	Pyrazolobenzodiazepines as cdk2 inhibitors

Country Status (33)

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US (3)	US6440959B1 (ko)
EP (1)	EP1185529B1 (ko)
JP (1)	JP3746680B2 (ko)
KR (1)	KR100481757B1 (ko)
CN (2)	CN1196703C (ko)
AR (1)	AR023542A1 (ko)
AT (1)	ATE279413T1 (ko)
AU (1)	AU768667B2 (ko)
BR (1)	BR0009887A (ko)
CA (1)	CA2367704C (ko)
CO (1)	CO5170444A1 (ko)
CZ (1)	CZ20013738A3 (ko)
DE (1)	DE60014893T2 (ko)
DK (1)	DK1185529T3 (ko)
ES (1)	ES2228522T3 (ko)
HK (1)	HK1046278B (ko)
HR (1)	HRP20010742A2 (ko)
HU (1)	HUP0300318A3 (ko)
IL (1)	IL145764A0 (ko)
JO (1)	JO2248B1 (ko)
MA (1)	MA26782A1 (ko)
NO (1)	NO20015065D0 (ko)
NZ (1)	NZ514523A (ko)
PE (1)	PE20010054A1 (ko)
PL (1)	PL200933B1 (ko)
PT (1)	PT1185529E (ko)
RU (1)	RU2249593C2 (ko)
SI (1)	SI1185529T1 (ko)
TR (1)	TR200103016T2 (ko)
TW (1)	TW585866B (ko)
WO (1)	WO2000064900A1 (ko)
YU (1)	YU73101A (ko)
ZA (1)	ZA200108016B (ko)

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NZ532463A (en) *	2001-11-13	2007-02-23	Dimensional Pharm Inc	Substituted 1,4-benzodiazepines and uses thereof for the treatment of cancer
FR2847253B1 (fr) *	2002-11-19	2007-05-18	Aventis Pharma Sa	Nouveaux derives de pyridazinones a titre de medicaments et compositions pharmaceutiques les renfermant
WO2004076424A1 (en) *	2003-02-27	2004-09-10	Abbott Laboratories	Heterocyclic kinase inhibitors
PL1802625T3 (pl) *	2004-10-13	2008-12-31	Hoffmann La Roche	Dwupodstawione pirazolobenzodiazepiny użyteczne jako inhibitory CDK2 i angiogenezy oraz w leczeniu raka sutka, okrężnicy, płuca i gruczołu krokowego
EP1940410A1 (en) *	2005-10-14	2008-07-09	F.Hoffmann-La Roche Ag	Regimen of administration for 5-(2-chlorophenyl)-1 ,2-dihydro-7-fluoro-8-methoxy-3-methyl-pyrazolo [3, 4.-b] [1, 4] benzodiazepine
EP2081921B1 (en)	2006-07-10	2010-09-08	PAION UK Limited	Short-acting benzodiazepine salts and their polymorphic forms
KR20100073454A (ko) *	2008-12-23	2010-07-01	국립암센터	트란스글루타미나제 억제제로 사용되는 신규한 피라졸로디아제핀계 화합물, 이의 제조방법 및 이를 포함하는 조성물
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HK1046278A1 (en)	2003-01-03
NO20015065L (no)	2001-10-18
CN1348455A (zh)	2002-05-08
CN1603314A (zh)	2005-04-06
CO5170444A1 (es)	2002-06-27
EP1185529A1 (en)	2002-03-13
HUP0300318A3 (en)	2004-11-29
AU768667B2 (en)	2003-12-18
YU73101A (sh)	2004-05-12
BR0009887A (pt)	2002-01-22
CA2367704A1 (en)	2000-11-02
NO20015065D0 (no)	2001-10-18
US6440959B1 (en)	2002-08-27
PL354405A1 (en)	2004-01-12
MA26782A1 (fr)	2004-12-20
SI1185529T1 (en)	2005-02-28
EP1185529B1 (en)	2004-10-13
RU2249593C2 (ru)	2005-04-10
DE60014893D1 (de)	2004-11-18
CN1196703C (zh)	2005-04-13
JP3746680B2 (ja)	2006-02-15
JO2248B1 (en)	2004-10-07
AU4748000A (en)	2000-11-10
CN1279029C (zh)	2006-10-11
AR023542A1 (es)	2002-09-04
ZA200108016B (en)	2003-03-26
KR20010112435A (ko)	2001-12-20
CA2367704C (en)	2008-06-17
PL200933B1 (pl)	2009-02-27
DE60014893T2 (de)	2005-10-13
ES2228522T3 (es)	2005-04-16
JP2002543081A (ja)	2002-12-17
US20040198976A1 (en)	2004-10-07
US6838558B2 (en)	2005-01-04
DK1185529T3 (da)	2005-02-07
US20020183514A1 (en)	2002-12-05
WO2000064900A1 (en)	2000-11-02
CZ20013738A3 (cs)	2002-08-14
TR200103016T2 (tr)	2002-04-22
HUP0300318A2 (hu)	2003-06-28
US6916923B2 (en)	2005-07-12
PT1185529E (pt)	2005-02-28
IL145764A0 (en)	2002-07-25
PE20010054A1 (es)	2001-02-07
TW585866B (en)	2004-05-01
HK1046278B (zh)	2005-08-12
NZ514523A (en)	2003-11-28
KR100481757B1 (ko)	2005-04-11

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