SG187548A1 - New aminopyrazoloquinazolines - Google Patents

Info

Publication number

SG187548A1

SG187548A1 SG2013003645A SG2013003645A SG187548A1 SG 187548 A1 SG187548 A1 SG 187548A1 SG 2013003645 A SG2013003645 A SG 2013003645A SG 2013003645 A SG2013003645 A SG 2013003645A SG 187548 A1 SG187548 A1 SG 187548A1

Authority

SG

Singapore

Prior art keywords

denotes

methyl

dihydropyrazolo

quinazolin

salkyl

Prior art date

2010-07-23

Links

• Espacenet
• Global Dossier
• Discuss

• SUOYKOLHSZCPPT-UHFFFAOYSA-N C1=CC2=NN=CC2=C2NC(N)=NC=C21 Chemical class C1=CC2=NN=CC2=C2NC(N)=NC=C21 SUOYKOLHSZCPPT-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 184
• 238000011282 treatment Methods 0.000 claims abstract description 14
• 239000003814 drug Substances 0.000 claims abstract description 6
• 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 6
• -1 1-aza-bicyclo[2.2.2]octyl Chemical group 0.000 claims description 218
• 238000000034 method Methods 0.000 claims description 114
• 229910052739 hydrogen Inorganic materials 0.000 claims description 81
• 239000001257 hydrogen Substances 0.000 claims description 76
• 125000000623 heterocyclic group Chemical group 0.000 claims description 70
• 229910052736 halogen Inorganic materials 0.000 claims description 67
• 150000002367 halogens Chemical class 0.000 claims description 67
• 125000001072 heteroaryl group Chemical group 0.000 claims description 60
• 125000001424 substituent group Chemical group 0.000 claims description 58
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 48
• 206010028980 Neoplasm Diseases 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 31
• 150000002431 hydrogen Chemical class 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 125000000217 alkyl group Chemical group 0.000 claims description 25
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
• 239000013543 active substance Substances 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 239000000203 mixture Substances 0.000 claims description 20
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 19
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 16
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 201000011510 cancer Diseases 0.000 claims description 13
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 10
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 10
• 230000002265 prevention Effects 0.000 claims description 10
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
• 239000000969 carrier Substances 0.000 claims description 7
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 7
• 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 6
• 239000005864 Sulphur Substances 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 125000002393 azetidinyl group Chemical group 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 5
• 239000000824 cytostatic agent Substances 0.000 claims description 4
• 230000001085 cytostatic effect Effects 0.000 claims description 4
• 208000023275 Autoimmune disease Diseases 0.000 claims description 3
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 231100000433 cytotoxic Toxicity 0.000 claims description 3
• 230000001472 cytotoxic effect Effects 0.000 claims description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 3
• ITTIOCBORUGHNT-UHFFFAOYSA-N 8-methyl-9-phenyl-n-[1-(2-piperazin-1-ylethyl)pyrazol-3-yl]-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound N1=C2C3=C(C=4C=CC=CC=4)N(C)N=C3CCC2=CN=C1NC(=N1)C=CN1CCN1CCNCC1 ITTIOCBORUGHNT-UHFFFAOYSA-N 0.000 claims description 2
• QXNWQMXMRDSICW-UHFFFAOYSA-N 8-methyl-9-phenyl-n-[1-(2-pyrrolidin-1-ylethyl)pyrazol-3-yl]-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound N1=C2C3=C(C=4C=CC=CC=4)N(C)N=C3CCC2=CN=C1NC(=N1)C=CN1CCN1CCCC1 QXNWQMXMRDSICW-UHFFFAOYSA-N 0.000 claims description 2
• YQZQYYJJDVEIMT-UHFFFAOYSA-N 8-methyl-n-[1-[2-(4-methylpiperazin-1-yl)ethyl]pyrazol-3-yl]-9-phenyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound C1CN(C)CCN1CCN1N=C(NC=2N=C3C4=C(N(C)N=C4CCC3=CN=2)C=2C=CC=CC=2)C=C1 YQZQYYJJDVEIMT-UHFFFAOYSA-N 0.000 claims description 2
• LMPVIPNEQZEESQ-UHFFFAOYSA-N 9-(2-chlorophenyl)-5,8-dimethyl-n-(1-methylpyrazol-3-yl)-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound N=1C=C2C(C)CC3=NN(C)C(C=4C(=CC=CC=4)Cl)=C3C2=NC=1NC=1C=CN(C)N=1 LMPVIPNEQZEESQ-UHFFFAOYSA-N 0.000 claims description 2
• PYAPIUCFOKEWID-UHFFFAOYSA-N 9-(2-chlorophenyl)-5,8-dimethyl-n-(1-propan-2-ylpyrazol-3-yl)-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound CC(C)N1C=CC(NC=2N=C3C4=C(N(C)N=C4CC(C)C3=CN=2)C=2C(=CC=CC=2)Cl)=N1 PYAPIUCFOKEWID-UHFFFAOYSA-N 0.000 claims description 2
• ALLOBHVKDVTDHL-UHFFFAOYSA-N 9-(2-chlorophenyl)-n-(1-ethylpyrazol-3-yl)-8-methyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound CCN1C=CC(NC=2N=C3C4=C(N(C)N=C4CCC3=CN=2)C=2C(=CC=CC=2)Cl)=N1 ALLOBHVKDVTDHL-UHFFFAOYSA-N 0.000 claims description 2
• REJXPVDGVBXCKX-UHFFFAOYSA-N 9-(2-chlorophenyl)-n-[2-methoxy-4-(4-methylpiperazin-1-yl)phenyl]-5,8-dimethyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=C1C2=3)=NC=C1C(C)CC2=NN(C)C=3C1=CC=CC=C1Cl REJXPVDGVBXCKX-UHFFFAOYSA-N 0.000 claims description 2
• OANOCAREUKJQGL-UHFFFAOYSA-N 9-(3-chlorothiophen-2-yl)-n-[1-(2-methoxyethyl)pyrazol-3-yl]-8-methyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound COCCN1C=CC(NC=2N=C3C4=C(C5=C(C=CS5)Cl)N(C)N=C4CCC3=CN=2)=N1 OANOCAREUKJQGL-UHFFFAOYSA-N 0.000 claims description 2
• JVFQUDUBMHESGO-UHFFFAOYSA-N 9-(4-chlorophenyl)-n-[1-(2-methoxyethyl)pyrazol-3-yl]-8-methyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound COCCN1C=CC(NC=2N=C3C4=C(N(C)N=C4CCC3=CN=2)C=2C=CC(Cl)=CC=2)=N1 JVFQUDUBMHESGO-UHFFFAOYSA-N 0.000 claims description 2
• JXHDHEYUVSBREH-UHFFFAOYSA-N 9-[(2-chlorophenyl)methyl]-n-(1-ethylpyrazol-3-yl)-8-methyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound CCN1C=CC(NC=2N=C3C4=C(CC=5C(=CC=CC=5)Cl)N(C)N=C4CCC3=CN=2)=N1 JXHDHEYUVSBREH-UHFFFAOYSA-N 0.000 claims description 2
• RXKJPJYJBMDEDC-UHFFFAOYSA-N 9-[(2-chlorophenyl)methyl]-n-[1-(2-methoxyethyl)pyrazol-3-yl]-8-methyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound COCCN1C=CC(NC=2N=C3C4=C(CC=5C(=CC=CC=5)Cl)N(C)N=C4CCC3=CN=2)=N1 RXKJPJYJBMDEDC-UHFFFAOYSA-N 0.000 claims description 2
• FFCMYRMLUZWDAB-UHFFFAOYSA-N 9-[(2-chlorophenyl)methyl]-n-[1-[2-(dimethylamino)ethyl]pyrazol-3-yl]-8-methyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound CN(C)CCN1C=CC(NC=2N=C3C4=C(CC=5C(=CC=CC=5)Cl)N(C)N=C4CCC3=CN=2)=N1 FFCMYRMLUZWDAB-UHFFFAOYSA-N 0.000 claims description 2
• SQFGKEFPEUHWJA-UHFFFAOYSA-N 9-[(3-methoxyphenyl)methyl]-8-methyl-n-(1-methylpyrazol-3-yl)-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound COC1=CC=CC(CC=2N(N=C3C=2C2=NC(NC4=NN(C)C=C4)=NC=C2CC3)C)=C1 SQFGKEFPEUHWJA-UHFFFAOYSA-N 0.000 claims description 2
• LDLJWKVRPLQFLD-UHFFFAOYSA-N 9-[4-(difluoromethoxy)phenyl]-n-(1-ethylpyrazol-3-yl)-8-methyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound CCN1C=CC(NC=2N=C3C4=C(N(C)N=C4CCC3=CN=2)C=2C=CC(OC(F)F)=CC=2)=N1 LDLJWKVRPLQFLD-UHFFFAOYSA-N 0.000 claims description 2
• CJHPZHXUFVNHAN-UHFFFAOYSA-N 9-[4-(difluoromethoxy)phenyl]-n-[1-(2-methoxyethyl)pyrazol-3-yl]-8-methyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound COCCN1C=CC(NC=2N=C3C4=C(N(C)N=C4CCC3=CN=2)C=2C=CC(OC(F)F)=CC=2)=N1 CJHPZHXUFVNHAN-UHFFFAOYSA-N 0.000 claims description 2
• SXALUXHTCNSKEQ-UHFFFAOYSA-N 9-[4-(difluoromethoxy)phenyl]-n-[1-[2-(dimethylamino)ethyl]pyrazol-3-yl]-8-methyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound CN(C)CCN1C=CC(NC=2N=C3C4=C(N(C)N=C4CCC3=CN=2)C=2C=CC(OC(F)F)=CC=2)=N1 SXALUXHTCNSKEQ-UHFFFAOYSA-N 0.000 claims description 2
• LXBKQBAEPHHFAV-UHFFFAOYSA-N 9-[4-(difluoromethoxy)phenyl]-n-[1-[2-(dimethylamino)ethyl]pyrazol-4-yl]-8-methyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound C1=NN(CCN(C)C)C=C1NC1=NC=C(CCC=2C3=C(N(C)N=2)C=2C=CC(OC(F)F)=CC=2)C3=N1 LXBKQBAEPHHFAV-UHFFFAOYSA-N 0.000 claims description 2
• UMKZMPIUCLGAOL-UHFFFAOYSA-N 9-benzyl-n-[1-[2-(dimethylamino)ethyl]pyrazol-3-yl]-8-methyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound CN(C)CCN1C=CC(NC=2N=C3C4=C(CC=5C=CC=CC=5)N(C)N=C4CCC3=CN=2)=N1 UMKZMPIUCLGAOL-UHFFFAOYSA-N 0.000 claims description 2
• 206010061218 Inflammation Diseases 0.000 claims description 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 claims description 2
• 208000015181 infectious disease Diseases 0.000 claims description 2
• 230000004054 inflammatory process Effects 0.000 claims description 2
• NTQFNBBTNKJHDU-UHFFFAOYSA-N n-(1-ethylpyrazol-3-yl)-8-methyl-9-[(3-methylphenyl)methyl]-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound CCN1C=CC(NC=2N=C3C4=C(CC=5C=C(C)C=CC=5)N(C)N=C4CCC3=CN=2)=N1 NTQFNBBTNKJHDU-UHFFFAOYSA-N 0.000 claims description 2
• ARWPUMUNJQFGGQ-UHFFFAOYSA-N n-[1-(2-methoxyethyl)pyrazol-3-yl]-5,8-dimethyl-9-phenyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound COCCN1C=CC(NC=2N=C3C4=C(N(C)N=C4CC(C)C3=CN=2)C=2C=CC=CC=2)=N1 ARWPUMUNJQFGGQ-UHFFFAOYSA-N 0.000 claims description 2
• AHPVVVDWNNYPQV-UHFFFAOYSA-N n-[1-(2-methoxyethyl)pyrazol-3-yl]-8-methyl-9-[(2-methylphenyl)methyl]-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound COCCN1C=CC(NC=2N=C3C4=C(CC=5C(=CC=CC=5)C)N(C)N=C4CCC3=CN=2)=N1 AHPVVVDWNNYPQV-UHFFFAOYSA-N 0.000 claims description 2
• LWQUHXAZSAMKHS-UHFFFAOYSA-N n-[1-(2-methoxyethyl)pyrazol-3-yl]-8-methyl-9-[(3-methylphenyl)methyl]-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound COCCN1C=CC(NC=2N=C3C4=C(CC=5C=C(C)C=CC=5)N(C)N=C4CCC3=CN=2)=N1 LWQUHXAZSAMKHS-UHFFFAOYSA-N 0.000 claims description 2
• DRJYVDSVFZZZEI-UHFFFAOYSA-N n-[1-[2-(dimethylamino)ethyl]pyrazol-3-yl]-5,8-dimethyl-9-phenyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound N=1C=C2C(C)CC3=NN(C)C(C=4C=CC=CC=4)=C3C2=NC=1NC=1C=CN(CCN(C)C)N=1 DRJYVDSVFZZZEI-UHFFFAOYSA-N 0.000 claims description 2
• NBFAIVQSUUURKB-UHFFFAOYSA-N n-[1-[2-(dimethylamino)ethyl]pyrazol-3-yl]-8-methyl-9-(3-methylthiophen-2-yl)-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound CN(C)CCN1C=CC(NC=2N=C3C4=C(C5=C(C=CS5)C)N(C)N=C4CCC3=CN=2)=N1 NBFAIVQSUUURKB-UHFFFAOYSA-N 0.000 claims description 2
• BRNVYLKWNJBOAJ-UHFFFAOYSA-N n-[1-[2-(dimethylamino)ethyl]pyrazol-3-yl]-8-methyl-9-(naphthalen-1-ylmethyl)-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound CN(C)CCN1C=CC(NC=2N=C3C4=C(CC=5C6=CC=CC=C6C=CC=5)N(C)N=C4CCC3=CN=2)=N1 BRNVYLKWNJBOAJ-UHFFFAOYSA-N 0.000 claims description 2
• QKFHSJDLWFPOMT-UHFFFAOYSA-N n-[1-[2-(dimethylamino)ethyl]pyrazol-3-yl]-8-methyl-9-phenyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound CN(C)CCN1C=CC(NC=2N=C3C4=C(N(C)N=C4CCC3=CN=2)C=2C=CC=CC=2)=N1 QKFHSJDLWFPOMT-UHFFFAOYSA-N 0.000 claims description 2
• LOFUVYKJPBSYDP-UHFFFAOYSA-N n-[1-[2-[2-methoxyethyl(methyl)amino]ethyl]pyrazol-3-yl]-8-methyl-9-phenyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound COCCN(C)CCN1C=CC(NC=2N=C3C4=C(N(C)N=C4CCC3=CN=2)C=2C=CC=CC=2)=N1 LOFUVYKJPBSYDP-UHFFFAOYSA-N 0.000 claims description 2
• HYLUAZCXPZMUBL-UHFFFAOYSA-N n-[1-[2-[4-(2-methoxyethyl)piperazin-1-yl]ethyl]pyrazol-3-yl]-8-methyl-9-phenyl-5,6-dihydropyrazolo[3,4-h]quinazolin-2-amine Chemical compound C1CN(CCOC)CCN1CCN1N=C(NC=2N=C3C4=C(N(C)N=C4CCC3=CN=2)C=2C=CC=CC=2)C=C1 HYLUAZCXPZMUBL-UHFFFAOYSA-N 0.000 claims description 2
• NIOSVSUQTYFZQG-UHFFFAOYSA-N quinazolin-2-amine Chemical compound C1=C=CC=C2[N]C(N)=NC=C21 NIOSVSUQTYFZQG-UHFFFAOYSA-N 0.000 claims 1
• 230000004663 cell proliferation Effects 0.000 abstract description 9
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• 125000000392 cycloalkenyl group Chemical group 0.000 description 14
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